Gemeprost

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

MedKoo CAT#: 461867

CAS#: 64318-79-2

Description: Gemeprost is an analogue of prostaglandin E1 and is used as a treatment for obstetric bleeding. It is used with mifepristone to terminate pregnancy up to 24 weeks gestation.


Price and Availability

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Gemeprost is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461867
Name: Gemeprost
CAS#: 64318-79-2
Chemical Formula: C23H38O5
Exact Mass: 394.2719
Molecular Weight: 394.55
Elemental Analysis: C, 70.02; H, 9.71; O, 20.27


Synonym: Gemeprost; Carprost; Cervagem; Gemeprostum; Preglandin; SC 37681; SC-37681; SC37681;

IUPAC/Chemical Name: methyl (E)-7-((1R,2R,3R)-3-hydroxy-2-((R,E)-3-hydroxy-4,4-dimethyloct-1-en-1-yl)-5-oxocyclopentyl)hept-2-enoate

InChi Key: KYBOHGVERHWSSV-VNIVIJDLSA-N

InChi Code: InChI=1S/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13+/t17-,18-,20-,21-/m1/s1

SMILES Code: CCCCC(C)(C)[C@H](O)/C=C/[C@@H]1[C@H](C(C[C@H]1O)=O)CCCC/C=C/C(OC)=O


Technical Data

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:
>3 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).

Harmonized System Code:
2934.99.03.00


References

1: Di Carlo C, Savoia F, Morra I, Ferrara C, Sglavo G, Nappi C. Effects of a prolonged, 72 hours, interval between mifepristone and gemeprost in second trimester termination of pregnancy: a retrospective analysis. Gynecol Endocrinol. 2014 Aug;30(8):605-7. doi: 10.3109/09513590.2014.930123. Epub 2014 Jun 6. PubMed PMID: 24905726.

2: La Torre R, Bevilacqua E, D'Ambrosio V, Pasquali G, Aliberti C, Perrone G, Giancotti A. A case of uterine rupture in mid-trimester spontaneous abortion: a complication of gemeprost vaginal administration. Clin Exp Obstet Gynecol. 2014;41(5):599-600. PubMed PMID: 25864271.

3: Domröse CM, Geipel A, Berg C, Lorenzen H, Gembruch U, Willruth A. Second- and third-trimester termination of pregnancy in women with uterine scar - a retrospective analysis of 111 gemeprost-induced terminations of pregnancy after previous cesarean delivery. Contraception. 2012 Jun;85(6):589-94. doi: 10.1016/j.contraception.2011.10.005. Epub 2011 Nov 12. PubMed PMID: 22079607.

4: Wong KS, Ngai CS, Wong AY, Tang LC, Ho PC. Vaginal misoprostol compared with vaginal gemeprost in termination of second trimester pregnancy. A randomized trial. Contraception. 1998 Oct;58(4):207-10. PubMed PMID: 9866000.

5: Henry AM, Haukkamaa M. Comparison of vaginal misoprostol and gemeprost as pre-treatment in first trimester pregnancy interruption. Br J Obstet Gynaecol. 1999 Jun;106(6):540-3. PubMed PMID: 10426610.

6: Celentano C, Prefumo F, Di Andrea O, Presti F, Di Nisio Q, Rotmensch S. Oral misoprostol vs. vaginal gemeprost prior to surgical termination of pregnancy in nulliparae. Acta Obstet Gynecol Scand. 2004 Aug;83(8):764-8. PubMed PMID: 15255850.

7: Thong KJ, Lynch P, Baird DT. A randomised study of two doses of gemeprost in combination with mifepristone for induction of abortion in the second trimester of pregnancy. Contraception. 1996 Aug;54(2):97-100. PubMed PMID: 8842586.

8: Norman JE, Thong KJ, Rodger MW, Baird DT. Medical abortion in women of less than or equal to 56 days amenorrhoea: a comparison between gemeprost (a PGE1 analogue) alone and mifepristone and gemeprost. Br J Obstet Gynaecol. 1992 Jul;99(7):601-6. PubMed PMID: 1525104.

9: Kai K, Karakida S, Kono M, Sasaki T, Togo K, Tsuno A, Nishida Y, Narahara H. Effects of parity and gestational age on second-trimester induction-abortion interval in combination with osmotic dilators and gemeprost. Contraception. 2012 Aug;86(2):147-52. doi: 10.1016/j.contraception.2011.11.016. Epub 2012 Jan 5. PubMed PMID: 22225843.

10: Tang OS, Thong KJ, Baird DT. Second trimester medical abortion with mifepristone and gemeprost: a review of 956 cases. Contraception. 2001 Jul;64(1):29-32. PubMed PMID: 11535210.

11: Scioscia M, Vimercati A, Doria G, Cuccovillo A, Lezzi V, Lacerenza A, Piro V, Greco P. [Second trimester termination of pregnancy with gemeprost: a review of 306 cases]. Minerva Ginecol. 2003 Aug;55(4):347-51. Italian. PubMed PMID: 14581859.

12: Nakayama D, Masuzaki H, Miura K, Hiraki K, Yoshimura S, Ishimaru T. Effect of placenta previa on blood loss in second-trimester abortion by labor induction using gemeprost. Contraception. 2007 Mar;75(3):238-40. Epub 2007 Jan 16. PubMed PMID: 17303496.

13: Gemzell-Danielsson K, Ostlund E. Termination of second trimester pregnancy with mifepristone and gemeprost. The clinical experience of 197 consecutive cases. Acta Obstet Gynecol Scand. 2000 Aug;79(8):702-6. PubMed PMID: 10949238.

14: Eppel W, Facchinetti F, Schleussner E, Piccinini F, Pizzi C, Gruber DM, Schneider B, Tschugguel W. Second trimester abortion using isosorbide mononitrate in addition to gemeprost compared with gemeprost alone: a double-blind randomized, placebo-controlled multicenter trial. Am J Obstet Gynecol. 2005 Mar;192(3):856-61. PubMed PMID: 15746682.

15: Ekerhovd E, Radulovic N, Norström A. Gemeprost versus misoprostol for cervical priming before first-trimester abortion: a randomized controlled trial. Obstet Gynecol. 2003 Apr;101(4):722-5. PubMed PMID: 12681876.

16: Craig S, Chau H, Cho H. Treatment of severe postpartum hemorrhage by rectally administered gemeprost pessaries. J Perinat Med. 1999;27(3):231-5. PubMed PMID: 10503187.

17: Wong KS, Ngai CS, Chan KS, Tang LC, Ho PC. Termination of second trimester pregnancy with gemeprost and misoprostol: a randomized double-blind placebo-controlled trial. Contraception. 1996 Jul;54(1):23-5. PubMed PMID: 8804804.

18: Thong KJ, Baird DT. Induction of second trimester abortion with mifepristone and gemeprost. Br J Obstet Gynaecol. 1993 Aug;100(8):758-61. PubMed PMID: 8399016.

19: Thong KJ, Baird DT. A study of gemeprost alone, dilapan or mifepristone in combination with gemeprost for the termination of second trimester pregnancy. Contraception. 1992 Jul;46(1):11-7. PubMed PMID: 1424619.

20: Bartley J, Brown A, Elton R, Baird DT. Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation. Hum Reprod. 2001 Oct;16(10):2098-102. PubMed PMID: 11574498.