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MedKoo Cat#: 540210 | Name: Hydroxyprogesterone caproate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Hydroxyprogesterone caproate is a synthetic ER antagonist used to prevent perterm birth.

Chemical Structure

Hydroxyprogesterone caproate
Hydroxyprogesterone caproate
CAS#630-56-8

Theoretical Analysis

MedKoo Cat#: 540210

Name: Hydroxyprogesterone caproate

CAS#: 630-56-8

Chemical Formula: C27H40O4

Exact Mass: 428.2927

Molecular Weight: 428.61

Elemental Analysis: C, 75.66; H, 9.41; O, 14.93

Price and Availability

Size Price Availability Quantity
500mg USD 250.00 2 Weeks
1g USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
17-((1-Oxohexyl)oxy)pregn-4-ene-3,20-dione; Delalutin; Idrogestene; Relutin; Syngynon
IUPAC/Chemical Name
(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl hexanoate
InChi Key
DOMWKUIIPQCAJU-LJHIYBGHSA-N
InChi Code
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
SMILES Code
CC([C@@]1(OC(CCCCC)=O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 428.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Mainiero AD, Rouse DJ, Lopes V, Hughes BL. Association of 17α-Hydroxyprogesterone Caproate and Risk of Infection. Obstet Gynecol. 2015 Jul;126(1):103-8. doi: 10.1097/AOG.0000000000000881. PubMed PMID: 26241262. 2: Zhao Y, Bettinger J, Caritis S, Venkataramanan R. Stability of hydroxyprogesterone caproate alone and in a compounded pharmaceutical product. Am J Health Syst Pharm. 2014 Jul 1;71(13):1120-7. doi: 10.2146/ajhp130466. PubMed PMID: 24939502. 3: Caritis SN, Venkataramanan R, Thom E, Harper M, Klebanoff MA, Sorokin Y, Thorp JM Jr, Varner MW, Wapner RJ, Iams JD, Carpenter MW, Grobman WA, Mercer BM, Sciscione A, Rouse DJ, Ramin S; Eunice Kennedy Shriver National Institute of Child Health and Human Development Maternal-Fetal Medicine Units Network and Obstetric-Fetal Pharmacology Research Units Network. Relationship between 17-alpha hydroxyprogesterone caproate concentration and spontaneous preterm birth. Am J Obstet Gynecol. 2014 Feb;210(2):128.e1-6. doi: 10.1016/j.ajog.2013.10.008. Epub 2013 Oct 7. PubMed PMID: 24113254; PubMed Central PMCID: PMC3926421. 4: Manuck TA, Esplin MS, Biggio J, Bukowski R, Parry S, Zhang H, Huang H, Varner MW, Andrews W, Saade G, Sadovsky Y, Reddy UM, Ilekis J; Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD) Genomics and Proteomics Network for Preterm Birth Research (GPN-PBR). Predictors of response to 17-alpha hydroxyprogesterone caproate for prevention of recurrent spontaneous preterm birth. Am J Obstet Gynecol. 2016 Mar;214(3):376.e1-8. doi: 10.1016/j.ajog.2015.12.010. Epub 2015 Dec 12. PubMed PMID: 26692181; PubMed Central PMCID: PMC4803498. 5: Stringer EM, Vladutiu CJ, Batra P, Stringer JS, Menard MK. Operationalizing 17α-Hydroxyprogesterone Caproate to Prevent Recurrent Preterm Birth: Definitions, Barriers, and Next Steps. Obstet Gynecol. 2016 Dec;128(6):1397-1402. PubMed PMID: 27824772. 6: O'Brien JM, Lewis DF. Prevention of preterm birth with vaginal progesterone or 17-alpha-hydroxyprogesterone caproate: a critical examination of efficacy and safety. Am J Obstet Gynecol. 2016 Jan;214(1):45-56. doi: 10.1016/j.ajog.2015.10.934. Epub 2015 Nov 10. Review. PubMed PMID: 26558340. 7: Stringer EM, Vladutiu CJ, Manuck T, Verbiest S, Ollendorff A, Stringer JS, Menard MK. 17-Hydroxyprogesterone caproate (17OHP-C) coverage among eligible women delivering at 2 North Carolina hospitals in 2012 and 2013: A retrospective cohort study. Am J Obstet Gynecol. 2016 Jul;215(1):105.e1-105.e12. doi: 10.1016/j.ajog.2016.01.180. Epub 2016 Jan 29. PubMed PMID: 26829508. 8: Manuck TA, Stoddard GJ, Fry RC, Esplin MS, Varner MW. Nonresponse to 17-alpha hydroxyprogesterone caproate for recurrent spontaneous preterm birth prevention: clinical prediction and generation of a risk scoring system. Am J Obstet Gynecol. 2016 Nov;215(5):622.e1-622.e8. doi: 10.1016/j.ajog.2016.07.013. Epub 2016 Jul 11. PubMed PMID: 27418444; PubMed Central PMCID: PMC5086280. 9: Rouholamin S, Zarean E, Sadeghi L. Evaluation the effect of 17-alpha hydroxyprogesterone caproate on gestational diabetes mellitus in pregnant women at risk for preterm birth. Adv Biomed Res. 2015 Oct 29;4:242. doi: 10.4103/2277-9175.168609. eCollection 2015. PubMed PMID: 26682208; PubMed Central PMCID: PMC4673703. 10: Saccone G, Suhag A, Berghella V. 17-alpha-hydroxyprogesterone caproate for maintenance tocolysis: a systematic review and metaanalysis of randomized trials. Am J Obstet Gynecol. 2015 Jul;213(1):16-22. doi: 10.1016/j.ajog.2015.01.054. Epub 2015 Feb 4. Review. PubMed PMID: 25659469. 11: Heyborne KD, Allshouse AA, Carey JC. Does 17-alpha hydroxyprogesterone caproate prevent recurrent preterm birth in obese women? Am J Obstet Gynecol. 2015 Dec;213(6):844.e1-6. doi: 10.1016/j.ajog.2015.08.014. Epub 2015 Aug 12. PubMed PMID: 26275354; PubMed Central PMCID: PMC4838905. 12: Stetson B, Hibbard JU, Wilkins I, Leftwich H. Outcomes With Cerclage Alone Compared With Cerclage Plus 17α-Hydroxyprogesterone Caproate. Obstet Gynecol. 2016 Nov;128(5):983-988. PubMed PMID: 27741201. 13: Romero R, Conde-Agudelo A. Is 17α-hydroxyprogesterone caproate contraindicated in twin gestations? BJOG. 2015 Jan;122(1):6-7. doi: 10.1111/1471-0528.13066. Epub 2014 Oct 3. PubMed PMID: 25280114. 14: Winer N, Bretelle F, Senat MV, Bohec C, Deruelle P, Perrotin F, Connan L, Vayssière C, Langer B, Capelle M, Azimi S, Porcher R, Rozenberg P; Groupe de Recherche en Obstétrique et Gynécologie. 17 alpha-hydroxyprogesterone caproate does not prolong pregnancy or reduce the rate of preterm birth in women at high risk for preterm delivery and a short cervix: a randomized controlled trial. Am J Obstet Gynecol. 2015 Apr;212(4):485.e1-485.e10. doi: 10.1016/j.ajog.2014.10.1097. Epub 2014 Oct 30. PubMed PMID: 25448515. 15: Orsulak MK, Block-Abraham D, Gee RE. 17α-hydroxyprogesterone caproate access in the Louisiana Medicaid population. Clin Ther. 2015 Apr 1;37(4):727-32. doi: 10.1016/j.clinthera.2015.01.007. Epub 2015 Feb 17. PubMed PMID: 25700945. 16: Combs CA, Garite TJ, Maurel K, Abril D, Das A, Clewell W, Heyborne K, How H, Huang W, Lewis D, Lu G, Miller H, Nageotte M, Porreco R, Sheikh A, Tran L; Obstetrix Collaborative Research Network. 17-hydroxyprogesterone caproate for preterm rupture of the membranes: a multicenter, randomized, double-blind, placebo-controlled trial. Am J Obstet Gynecol. 2015 Sep;213(3):364.e1-12. doi: 10.1016/j.ajog.2015.05.009. Epub 2015 May 13. PubMed PMID: 25979614. 17: Chang J, Zhao Y, Zhao W, Venkataramanan R, Caritis SN; Obstetrical-Fetal Pharmacology Research Units Network. Quality assessment of compounded 17-hydroxyprogesterone caproate. Am J Obstet Gynecol. 2014 Jan;210(1):47.e1-7. doi: 10.1016/j.ajog.2013.09.039. Epub 2013 Nov 4. PubMed PMID: 24200163; PubMed Central PMCID: PMC3939712. 18: Heyborne KD. 17-α Hydroxyprogesterone Caproate for the Prevention of Recurrent Preterm Birth: One Size May Not Fit All. Obstet Gynecol. 2016 Oct;128(4):899-903. doi: 10.1097/AOG.0000000000001618. PubMed PMID: 27607880. 19: Amaral LM, Cornelius DC, Harmon A, Moseley J, Martin JN Jr, LaMarca B. 17-hydroxyprogesterone caproate significantly improves clinical characteristics of preeclampsia in the reduced uterine perfusion pressure rat model. Hypertension. 2015 Jan;65(1):225-31. doi: 10.1161/HYPERTENSIONAHA.114.04484. Epub 2014 Nov 3. PubMed PMID: 25368030; PubMed Central PMCID: PMC4350787. 20: Manuck TA, Watkins WS, Moore B, Esplin MS, Varner MW, Jackson GM, Yandell M, Jorde L. Pharmacogenomics of 17-alpha hydroxyprogesterone caproate for recurrent preterm birth prevention. Am J Obstet Gynecol. 2014 Apr;210(4):321.e1-321.e21. doi: 10.1016/j.ajog.2014.01.013. Epub 2014 Mar 1. PubMed PMID: 24594138; PubMed Central PMCID: PMC4266558.

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