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630-56-8

630-56-8 | 17-Caproxyprogesterone

CAS No: 630-56-8 Catalog No: AG003DVP MDL No:MFCD00072134

Product Description

Catalog Number:
AG003DVP
Chemical Name:
17-Caproxyprogesterone
CAS Number:
630-56-8
Molecular Formula:
C27H40O4
Molecular Weight:
428.6041
MDL Number:
MFCD00072134
IUPAC Name:
[(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
InChI:
InChI=1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1
InChI Key:
DOMWKUIIPQCAJU-LJHIYBGHSA-N
SMILES:
CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C(=O)C
EC Number:
211-138-8
UNII:
276F2O42F5
NSC Number:
17592

Properties

Complexity:
797  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
0
Exact Mass:
428.293g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
428.613g/mol
Monoisotopic Mass:
428.293g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
60.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.7  

Literature

Title Journal
An in vitro approach for prioritization and evaluation of chemical effects on glucocorticoid receptor mediated adipogenesis. Toxicology and applied pharmacology 20180915
Clinical Application of Progesterone for the Prevention of Preterm Birth, 2016. American journal of perinatology 20160201
Prevention of preterm birth with vaginal progesterone or 17-alpha-hydroxyprogesterone caproate: a critical examination of efficacy and safety. American journal of obstetrics and gynecology 20160101
Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Seminars in perinatology 20141201
Systemic progesterone therapy--oral, vaginal, injections and even transdermal? Maturitas 20141101
Relationship between 17-hydroxyprogesterone caproate concentrations and gestational age at delivery in twin gestation. American journal of obstetrics and gynecology 20121101
Pharmacology and placental transport of 17-hydroxyprogesterone caproate in singleton gestation. American journal of obstetrics and gynecology 20121101
17 alpha-hydroxyprogesterone caproate to prevent prematurity in nulliparas with cervical length less than 30 mm. American journal of obstetrics and gynecology 20121101
The safety of progesterone and 17-hydroxyprogesterone caproate administration for the prevention of preterm birth: an evidence-based assessment. American journal of perinatology 20121001
Effect of 17-alpha hydroxyprogesterone caproate on cervical length in twin pregnancies. Ultrasound in obstetrics & gynecology : the official journal of the International Society of Ultrasound in Obstetrics and Gynecology 20121001
Pregnancy outcomes of women receiving compounded 17 α-hydroxyprogesterone caproate for prophylactic prevention of preterm birth 2004 to 2011. American journal of perinatology 20120901
Technique modifications for reducing the risks from amniocentesis or chorionic villus sampling. The Cochrane database of systematic reviews 20120815
Pregnancy outcomes of managed Medicaid members prescribed home administration of 17 α-hydroxyprogesterone caproate. American journal of perinatology 20120801
Source of 17-hydroxyprogesterone caproate in clinical trials. American journal of obstetrics and gynecology 20120801
Recurrent preterm birth in women treated with 17 α-hydroxyprogesterone caproate: the contribution of risk factors in the penultimate pregnancy. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20120701
The prediction of recurrent preterm birth in patients on 17-alpha-hydroxyprogesterone caproate using serial fetal fibronectin and cervical length. American journal of obstetrics and gynecology 20120701
Altered arterial stiffness in male-to-female transsexuals undergoing hormonal treatment. The journal of obstetrics and gynaecology research 20120601
Evidences for antinociceptive effect of 17-α-hydroxyprogesterone caproate in carpal tunnel syndrome. Journal of molecular neuroscience : MN 20120501
Quality investigation of hydroxyprogesterone caproate active pharmaceutical ingredient and injection. Drug development and industrial pharmacy 20120501
Trends in prematurity: what do changes at an urban institution suggest about the public health impact of 17-alpha hydroxyprogesterone caproate? Maternal and child health journal 20120401
Multigeneration reproductive study of hydroxyprogesterone caproate (HPC) in the rat: laboratory results and clinical significance. Birth defects research. Part B, Developmental and reproductive toxicology 20120401
Studies examine fetal surgery trade-offs, drug interactions, and uterine rupture. JAMA 20120328
Single dose 17 alpha-hydroxyprogesterone caproate in preterm labor: a randomized trial. Archives of gynecology and obstetrics 20120301
Metabolism of 17-alpha-hydroxyprogesterone caproate by human placental mitochondria. Reproductive sciences (Thousand Oaks, Calif.) 20120301
Prevention of preterm delivery after successful tocolysis in preterm labor by 17 alpha-hydroxyprogesterone caproate: a randomized controlled trial. American journal of obstetrics and gynecology 20120301
17α Hydroxyprogesterone caproate for prevention of recurrent spontaneous preterm birth. Reproductive toxicology (Elmsford, N.Y.) 20120101
17-α hydroxyprogesterone caproate for the prevention of preterm birth. Women's health (London, England) 20120101
Progestogens to prevent preterm birth in twin pregnancies: an individual participant data meta-analysis of randomized trials. BMC pregnancy and childbirth 20120101
Prevention and management of preterm birth. Journal of pregnancy 20120101
Drugs in traffic: the road to approval. Nature medicine 20111206
The rates of abnormal glucose challenge tests and gestational diabetes in women receiving 17α-hydroxyprogesterone caproate. American journal of perinatology 20111201
Iatrogenic autoimmune progesterone dermatitis caused by 17alpha-hydroxyprogesterone caproate for preterm labor prevention. Cutis 20111101
Efficacy of 17α-hydroxyprogesterone caproate in prevention of preterm delivery. The journal of obstetrics and gynaecology research 20111001
17 α-Hydroxyprogesterone caproate (Makena™): in the prevention of preterm birth. Paediatric drugs 20111001
Medical director to the rescue! Managed care (Langhorne, Pa.) 20111001
17α-hydroxyprogesterone caproate for the prevention of adverse neonatal outcome in multiple pregnancies: a randomized controlled trial. Obstetrics and gynecology 20110901
17-alphahydroxyprogesterone caproate in women with previous spontaneous preterm delivery: does a previous term delivery affect the rate of recurrence? American journal of obstetrics and gynecology 20110901
Influence of gestational age and reason for prior preterm birth on rates of recurrent preterm delivery. American journal of obstetrics and gynecology 20110901
Progesterone receptor polymorphisms and clinical response to 17-alpha-hydroxyprogesterone caproate. American journal of obstetrics and gynecology 20110801
Comparison of success rate of nifedipine, progesterone, and bed rest for inhibiting uterine contraction in threatened preterm labor. The journal of obstetrics and gynaecology research 20110701
Pharmacokinetics of 17-hydroxyprogesterone caproate in multifetal gestation. American journal of obstetrics and gynecology 20110701
Deus ex Makena? Obstetrics and gynecology 20110601
Unjustified increase in cost of care resulting from U.S. Food and Drug Administration approval of Makena (17α-hydroxyprogesterone caproate). Obstetrics and gynecology 20110601
What agent should be used to prevent recurrent preterm birth: 17-P or natural progesterone? Obstetrics and gynecology clinics of North America 20110601
What is in a name? A higher cost! South Dakota medicine : the journal of the South Dakota State Medical Association 20110601
17-hydroxyprogesterone caproate, progesterone, preterm birth prevention, and safety: who decides? Someone should. American journal of obstetrics and gynecology 20110501
The effect of 17α-hydroxyprogesterone caproate on preterm birth in women with an ultrasound-indicated cerclage. American journal of perinatology 20110501
17-hydroxyprogesterone caproate for twin pregnancy: a double-blind, randomized clinical trial. American journal of obstetrics and gynecology 20110301
The influence of prior obstetrical history on current 17-hydroxyprogesterone caproate use. Journal of pregnancy 20110101
Prevention of preterm labour: 2011 update on tocolysis. Journal of pregnancy 20110101
17-Hydroxyprogesterone caproate to prolong pregnancy after preterm rupture of the membranes: early termination of a double-blind, randomized clinical trial. BMC research notes 20110101
Second trimester cervical length and risk of preterm birth in women with twin gestations treated with 17-α hydroxyprogesterone caproate. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20101201
Intramuscular 17α-hydroxyprogesterone caproate administration attenuates immunoresponsiveness of maternal peripheral blood mononuclear cells. American journal of obstetrics and gynecology 20101201
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20101201
Using 17 α-hydroxyprogesterone caproate to impact rates of recurrent preterm delivery in clinical practice. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20101001
Effect of 17-alpha hydroxyprogesterone caproate on the production of tumor necrosis factor-alpha and the expression of cyclooxygenase-2 in lipopolysaccharide-treated gravid human myometrial explants. Journal of perinatology : official journal of the California Perinatal Association 20100901
17-alpha-hydroprogesterone caproate and cervical changes. American journal of obstetrics and gynecology 20100901
Metabolism of 17alpha-hydroxyprogesterone caproate, an agent for preventing preterm birth, by fetal hepatocytes. Drug metabolism and disposition: the biological fate of chemicals 20100501
17-alpha-hydroxyprogesterone caproate for the prevention of preterm birth in women with prior preterm birth and a short cervical length. American journal of obstetrics and gynecology 20100401
Uterine activity in women receiving 17 alpha-hydroxyprogesterone caproate for the prevention of preterm birth: an observational study. American journal of perinatology 20100201
Continuous infusion of 17-hydroxyprogesterone caproate into either the fetoplacental or intervillous circulation of a placental cotyledon attenuates vasoconstriction of the fetoplacental arteries by thromboxane mimetic U46619. American journal of obstetrics and gynecology 20100201
Omega-3 fatty acid supplementation to prevent recurrent preterm birth: a randomized controlled trial. Obstetrics and gynecology 20100201
Impact of 17P usage on NICU admissions in a managed medicaid population--a five-year review. Managed care (Langhorne, Pa.) 20100201
Expression of stretch-activated two-pore potassium channels in human myometrium in pregnancy and labor. PloS one 20100101
Hormonal therapy in advanced or recurrent endometrial cancer. The Cochrane database of systematic reviews 20100101
Fertility-preserving treatment in young women with well-differentiated endometrial carcinoma and severe atypical hyperplasia of endometrium. Fertility and sterility 20091201
The effect of treatment with 17 alpha-hydroxyprogesterone caproate on changes in cervical length over time. American journal of obstetrics and gynecology 20091001
The effect of 17-alpha hydroxyprogesterone caproate on the risk of gestational diabetes in singleton or twin pregnancies. American journal of obstetrics and gynecology 20091001
Effects of 17-hydroxyprogesterone on tumor necrosis factor-alpha-induced hypertension during pregnancy. American journal of hypertension 20091001
Pharmacological use of progesterone and 17-alpha-hydroxyprogesterone caproate in the prevention of preterm delivery. Minerva ginecologica 20091001
Progesterone does not prevent preterm births in women with twins. Southern medical journal 20090901
17-Hydroxyprogesterone blunts the hypertensive response associated with reductions in uterine perfusion pressure in pregnant rats. American journal of obstetrics and gynecology 20090901
Effect of 17alpha-hydroxyprogesterone caproate on glucose intolerance in pregnancy. Obstetrics and gynecology 20090701
Safety signals of 17-OHP-C use in pregnancy and efficacy in the prevention of preterm birth. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20090601
Folic acid supplementation and spontaneous preterm birth: adding grist to the mill? PLoS medicine 20090501
Prematurity in twin pregnancies. Minerva ginecologica 20090401
Discovery of selective glucocorticoid receptor modulators by multiplexed reporter screening. Proceedings of the National Academy of Sciences of the United States of America 20090324
Prevention of preterm birth in triplets using 17 alpha-hydroxyprogesterone caproate: a randomized controlled trial. Obstetrics and gynecology 20090201
Effect of oral N-acetyl cysteine on recurrent preterm labor following treatment for bacterial vaginosis. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics 20090101
A randomized trial of cerclage vs. 17 alpha-hydroxyprogesterone caproate for treatment of short cervix. Journal of perinatal medicine 20090101
The role of progesterone in prevention of preterm birth. International journal of women's health 20090101
Simultaneous quantitation of 17alpha-hydroxyprogesterone caproate, 17alpha-hydroxyprogesterone and progesterone in human plasma using high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS). Journal of pharmaceutical and biomedical analysis 20081201
Estrus induction and fertility rates in response to exogenous hormonal administration in postpartum anestrous and subestrus bovines and buffaloes. The Journal of veterinary medical science 20081201
Salivary progesterone and estriol among pregnant women treated with 17-alpha-hydroxyprogesterone caproate or placebo. American journal of obstetrics and gynecology 20081101
ACOG Committee Opinion number 419 October 2008 (replaces no. 291, November 2003). Use of progesterone to reduce preterm birth. Obstetrics and gynecology 20081001
Women receiving 17-alpha-hydroxyprogesterone caproate hospitalized for preterm labor at less than 34 weeks benefit from daily perinatal nursing surveillance. American journal of obstetrics and gynecology 20081001
17alpha-hydroxy-progesterone effects on cervical proinflammatory agents in women at risk for preterm delivery. American journal of perinatology 20080901
The impact of maternal body mass on the effectiveness of 17 alpha-hydroxyprogesterone caproate. The Journal of reproductive medicine 20080901
Transplacental transfer and metabolism of 17-alpha-hydroxyprogesterone caproate. American journal of obstetrics and gynecology 20080801
Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A 20080502
Effect of 17alpha-hydroxyprogesterone caproate before embryo transfer on the outcome of in vitro fertilization and embryo transfer: a randomized trial. Fertility and sterility 20080501
The use of 17 alpha-hydroxyprogesterone caproate (17p) in women with cervical cerclage. American journal of perinatology 20080501
The effect of esterases on 17alpha-hydroxyprogesterone caproate. American journal of obstetrics and gynecology 20080201
Progestational agents prevent preterm birth induced by a nitric oxide synthesis inhibitor in the mouse. In vivo (Athens, Greece) 20080101
Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins. American journal of obstetrics and gynecology 20071201
Progesterone and preterm birth. The New England journal of medicine 20071129
Follow-up of children exposed in utero to 17 alpha-hydroxyprogesterone caproate compared with placebo. Obstetrics and gynecology 20071001
Prophylaxis with 17 alpha-hydroxyprogesterone caproate for prevention of recurrent preterm delivery: does gestational age at initiation of treatment matter? American journal of obstetrics and gynecology 20070901
Clinical characteristics of women prescribed 17 alpha-hydroxyprogesterone caproate in the community setting. American journal of obstetrics and gynecology 20070901
A trial of 17 alpha-hydroxyprogesterone caproate to prevent prematurity in twins. The New England journal of medicine 20070802
Progesterone and preterm labor--still no definite answers. The New England journal of medicine 20070802
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17 Progesterone for preterm birth prevention: a potential 2 billion dollar opportunity. American journal of obstetrics and gynecology 20070301
Medical cost savings associated with 17 alpha-hydroxyprogesterone caproate. American journal of obstetrics and gynecology 20070301
Increased recurrence of preterm delivery with early cessation of 17-alpha-hydroxyprogesterone caproate. American journal of obstetrics and gynecology 20070301
Gestational age at initiation of 17-hydroxyprogesterone caproate (17P) and recurrent preterm delivery. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20070301
Embryo-fetal toxicity signals for 17alpha-hydroxyprogesterone caproate in high-risk pregnancies: a review of the non-clinical literature for embryo-fetal toxicity with progestins. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20070201
Progesterone for the prevention of preterm birth in women with multiple pregnancies: the AMPHIA trial. BMC pregnancy and childbirth 20070101
Inhibition of lipid peroxidation induced by hydroxyprogesterone caproate by some conventional antioxidants in goat liver homogenates. Acta poloniae pharmaceutica 20070101
Population-based case-control teratogenic study of hydroxyprogesterone treatment during pregnancy. Congenital anomalies 20061201
Massive pre-placental and subchorionic haematoma. Singapore medical journal 20061201
17-Hydroxyprogesterone caproate reverses induced vasoconstriction of the fetoplacental arteries by the thromboxane mimetic U46619. American journal of obstetrics and gynecology 20061001
The use of progestational agents for preterm birth: lessons from a mouse model. American journal of obstetrics and gynecology 20061001
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Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Detection of 17alpha-hydroxyprogesterone caproate in equine plasma by gas chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20060101
Role of progestogens for the prevention of premature birth. The Journal of steroid biochemistry and molecular biology 20051201
Prevention and treatment of pregnancy-induced hypertension (preeclampsia) with progestogens. The Journal of steroid biochemistry and molecular biology 20051201
Efficacy and safety of 17alpha-hydroxyprogesterone caproate in hormone replacement therapy. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20051101
17 alpha-hydroxyprogesterone caproate (17P) usage in a Medicaid managed care plan and reduction in neonatal intensive care unit days. Managed care (Langhorne, Pa.) 20051001
Does progesterone treatment influence risk factors for recurrent preterm delivery? Obstetrics and gynecology 20050901
Gestational exposure to hydroxyprogesterone caproate suppresses reproductive potential in male rats. Die Naturwissenschaften 20050801
Estimated effect of 17 alpha-hydroxyprogesterone caproate on preterm birth in the United States. Obstetrics and gynecology 20050201
Progestational agents to prevent preterm birth: a meta-analysis of randomized controlled trials. Obstetrics and gynecology 20050201
Hydroxyprogesterone caproate and progesterone increase tumor necrosis factor-alpha production in lipopolysaccharide stimulated whole blood from non-pregnant women. Journal of perinatal medicine 20050101
Transient parkinsonism: induced by progesterone or pregnancy? Movement disorders : official journal of the Movement Disorder Society 20041101
[Hormone therapy for uterine corpus cancer--introduction]. Nihon rinsho. Japanese journal of clinical medicine 20041001
[Conservative hormonal therapy for endometrial cancer]. Nihon rinsho. Japanese journal of clinical medicine 20041001
17 alpha-hydroxyprogesterone caproate versus intravaginal progesterone in IVF-embryo transfer cycles: a prospective randomized study. Reproductive biomedicine online 20040701
Impairment of male reproduction in adult rats exposed to hydroxyprogesterone caproate in utero. Die Naturwissenschaften 20040501
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ACOG Committee Opinion. Use of progesterone to reduce preterm birth. Obstetrics and gynecology 20031101
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[The effect of progestins on endometrial cancer in morphometric evaluation]. Ginekologia polska 20011201
A prospective randomized study comparing intramuscular progesterone and 17alpha-hydroxyprogesterone caproate in patients undergoing in vitro fertilization-embryo transfer cycles. Fertility and sterility 20010801
[Therapy of atypical hyperplasia and adenocarcinoma of the endometrium with the combination of progestins and anticoagulants]. Voprosy onkologii 20010101
Organ preserving method in the management of atypical endometrial hyperplasia. European journal of gynaecological oncology 20010101
Preliminary experience with steroidal ovarian suppression for prevention of severe ovarian hyperstimulation syndrome in IVF patients. Human fertility (Cambridge, England) 20010101
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[Comparison between the roles of aminoglutethimide and hydroxyprogesterone caproates in the treatment of endometrial cancer]. Zhonghua fu chan ke za zhi 19950801
Rapid increase in lumbar spine bone density in osteopenic women by high-dose intramuscular estrogen-progestogen injections. A preliminary report. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 19940901
Preferential expression of long form prolactin receptor mRNA in the rat brain during the oestrous cycle, pregnancy and lactation: hormones involved in its gene expression. The Journal of endocrinology 19940501
Studies on mechanisms and blockade of carcinogenic action of female sex hormones. Science in China. Series B, Chemistry, life sciences & earth sciences 19940401
[Changes in reproductive hormones levels in the treatment of endometrial precancerous lesion with hydroxyprogesterone caproate]. Zhonghua fu chan ke za zhi 19940401
Adjuvant progestagen therapy improves survival in patients with endometrial cancer after hysterectomy. Results of one-institutional prospective clinical trial. European journal of gynaecological oncology 19930101
Morphological aspects of the hormone-induced pathomorphosis of endometrial carcinoma. European journal of gynaecological oncology 19930101
Favourable influence of adjuvant hormone therapy by oxyprogesterone caproate (OPC) and by its combination with tamoxifen on 5-year survival rate of surgical and combined treatment of primary endometrial carcinoma patients. European journal of gynaecological oncology 19930101
Changes in fibronectin production in rat liver during cirrhotic evolution due to treatment with CCl4 and steroid hormones: correlation with plasmatic fibronectin. Pathologica 19920101
Progestogen administration in pregnancy may prevent preterm delivery. British journal of obstetrics and gynaecology 19900201
Effect of oxyprogesterone caproate, tamoxifen and their combination on the level of steroid hormone receptors in the tumor, and some parameters of the reproductive system in patients with endometrial cancer. Clinical and experimental obstetrics & gynecology 19900101
[Therapy of mastodynia and simple mastopathy]. Zentralblatt fur Gynakologie 19900101
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