MedKoo Cat#: 462868 | Name: Carboprost methyl
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Description:

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

Carboprost methyl is a synthetic prostaglandin analogue of PGF2α with oxytocic properties. Its main use is in the obstetrical emergency of postpartum hemorrhage which reduces postpartum bleeding during these circumstances. It is also a potent uterine stimulant and abortifacient.

Chemical Structure

Carboprost methyl
Carboprost methyl
CAS#35700-21-1 (methylated)

Theoretical Analysis

MedKoo Cat#: 462868

Name: Carboprost methyl

CAS#: 35700-21-1 (methylated)

Chemical Formula: C22H38O5

Exact Mass: 382.2719

Molecular Weight: 382.54

Elemental Analysis: C, 69.08; H, 10.01; O, 20.91

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
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Synonym
Methyl carboprost; U 36384; U36384; U-36384; U-36,384;
IUPAC/Chemical Name
methyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept-5-enoate
InChi Key
QQCOAAFKJZXJFP-XAYIDPIISA-N
InChi Code
InChI=1S/C22H38O5/c1-4-5-10-14-22(2,26)15-13-18-17(19(23)16-20(18)24)11-8-6-7-9-12-21(25)27-3/h6,8,13,15,17-20,23-24,26H,4-5,7,9-12,14,16H2,1-3H3/b8-6-,15-13+/t17-,18-,19+,20-,22+/m1/s1
SMILES Code
CCCCC[C@](O)(/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(OC)=O)O)O)C
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 382.54 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: Duan H, Hao M, Wang SM, Meng YJ, Wang Y, Yuan R, Xue X, Yang Q, Lin J, He YL, Shi YL, Liu JH, Wang X, Wang S. [Clinical multicenter study of carboprost methylate suppository for cervical ripening prior to diagnostic hysteroscopy]. Zhonghua Fu Chan Ke Za Zhi. 2018 Sep 25;53(9):602-607. Chinese. doi: 10.3760/cma.j.issn.0529-567x.2018.09.004. PMID: 30293295. 2: Tang PP, Hu HY, Gao JS, Hu J, Zhong YF, Wang T, Song YN, Zhou XY, Yang JQ, Liu JT, Pan J, Shi HF. [Evaluation of efficacy and safety of pelvic arterial embolization in women with primary postpartum hemorrhage]. Zhonghua Fu Chan Ke Za Zhi. 2016 Feb;51(2):81-6. Chinese. doi: 10.3760/cma.j.issn.0529-567X.2016.02.001. PMID: 26917474. 3: Quan ZF, Tian M, Chi P. Large doses of uterotonic drugs caused type II second degree sinoatrial block during cesarean section. Int J Clin Pharmacol Ther. 2016 Jan;54(1):62-4. doi: 10.5414/CP202453. PMID: 26636420. 4: Yin L, Meng X, Zhou X, Zhang T, Sun H, Yang Z, Yang B, Xiao N, Fawcett JP, Yang Y, Gu J. Simultaneous determination of carboprost methylate and its active metabolite carboprost in dog plasma by liquid chromatography-tandem mass spectrometry with positive/negative ion-switching electrospray ionization and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Aug 15;998-999:8-14. doi: 10.1016/j.jchromb.2015.05.039. Epub 2015 Jun 25. PMID: 26149245. 5: Hou SP, Chen OJ, Huang LH, Cheng LN, Teng YC. Medical methods for cervical ripening before the removal of intrauterine devices in postmenopausal women: a systematic review. Eur J Obstet Gynecol Reprod Biol. 2013 Jul;169(2):130-42. doi: 10.1016/j.ejogrb.2013.02.018. Epub 2013 Mar 14. PMID: 23497958. 6: Zou LY, Fan L. [Induced termination of second and third trimester pregnancy in women with scarred uterus]. Zhonghua Fu Chan Ke Za Zhi. 2010 Jan;45(1):17-21. Chinese. PMID: 20367920. 7: Vaid A, Dadhwal V, Mittal S, Deka D, Misra R, Sharma JB, Vimla N. A randomized controlled trial of prophylactic sublingual misoprostol versus intramuscular methyl-ergometrine versus intramuscular 15-methyl PGF2alpha in active management of third stage of labor. Arch Gynecol Obstet. 2009 Dec;280(6):893-7. doi: 10.1007/s00404-009-1019-y. Epub 2009 Mar 11. PMID: 19277690. 8: Sundaram S, Diaz JP, González-Quintero VH, Verma U. Rectal misoprostol vs 15-methyl prostaglandin F2alpha for retained placenta after second-trimester delivery. Am J Obstet Gynecol. 2009 May;200(5):e24-6. doi: 10.1016/j.ajog.2008.09.868. Epub 2009 Jan 10. PMID: 19136084. 9: Vimala N, Mittal S, Dadhwal V. Cervical priming with sublingual misoprostol vs. 15-methyl-prostaglandin F2alpha prior to surgical abortion. Int J Gynaecol Obstet. 2005 Feb;88(2):134-7. doi: 10.1016/j.ijgo.2004.10.010. Epub 2004 Dec 8. PMID: 15694088. 10: Rodríguez de la Torre MR, Gallego Alonso JI, Gil Fernández M. Edema pulmonar en una cesárea relacionado con la administración de 15-metil prostaglandina F2alpha [Pulmonary edema related to administration of 15-methyl-prostaglandin F2alpha during a cesarean section]. Rev Esp Anestesiol Reanim. 2004 Feb;51(2):104-7. Spanish. PMID: 15072404. 11: Yang Y, Tan D, Liu X. [Effect of methyl carboprost suppository in preventing postpartum hemorrhage: clinical observation]. Di Yi Jun Yi Da Xue Xue Bao. 2003 Jun;23(6):556. Chinese. PMID: 12868460. 12: Bozhinova S, Porozhanova V, Atanasova S, Tsvetkov M, Popovski K, Penkov V. Ratsionalen podkhod v upotrebata na prostaglandini pri sledrodova matochna khipotoniia [Rational method for prostaglandin use in cases with postpartal uterine hypotonia]. Akush Ginekol (Sofiia). 2001;40(3):15-9. Bulgarian. PMID: 11785359. 13: Lamont RF, Morgan DJ, Logue M, Gordon H. A prospective randomised trial to compare the efficacy and safety of hemabate and syntometrine for the prevention of primary postpartum haemorrhage. Prostaglandins Other Lipid Mediat. 2001 Oct;66(3):203-10. doi: 10.1016/s0090-6980(01)00154-x. PMID: 11577783. 14: Fait T, Calda P, Zizka Z, Pavlista D, Hrusková H, Zivný J. Ukoncení 128 tĕhotenství ve II. trimestru gravidity aplikací prostaglandinu 15 metyl F2alfa [Termination of 128 pregnancies in the 2nd trimester using prostaglandin 15 methyl F2 alpha]. Ceska Gynekol. 2000 Nov;65(6):451-5. Czech. PMID: 11272068. 15: Perry KG Jr, Rinehart BK, Terrone DA, Martin RW, May WL, Roberts WE. Second- trimester uterine evacuation: A comparison of intra-amniotic (15S)-15-methyl- prostaglandin F2alpha and intravaginal misoprostol. Am J Obstet Gynecol. 1999 Nov;181(5 Pt 1):1057-61. doi: 10.1016/s0002-9378(99)70081-5. PMID: 10561618. 16: Perry KG Jr, Roberts WE, Martin RW, Magann EF, Sullivan DL, Morrison JC. Comparison of intra-amniotic (15S)-15-methyl-PGF2 alpha and intravaginal prostaglandin E2 for second-trimester uterine evacuation. J Perinatol. 1998 Jan- Feb;18(1):24-7. PMID: 9527940. 17: Liu C, Wang D, Li X. [Clinical study on reduction of postpartum bleeding by methyl carprost suppository]. Zhonghua Fu Chan Ke Za Zhi. 1997 Jan;32(1):22-4. Chinese. PMID: 9596865. 18: Tang L, Zhu Q, Wang S. [Dose study of methyl carboprost suppository for planned delivery at term]. Zhonghua Fu Chan Ke Za Zhi. 1997 Jan;32(1):19-21. Chinese. PMID: 9596864. 19: Biswas A, Roy S. A comparative study of the efficacy and safety of synthetic prostaglandin E2 derivative and 15-methyl prostaglandin F2 alpha in the termination of midtrimester pregnancy. J Indian Med Assoc. 1996 Aug;94(8):292-3. PMID: 8855576. 20: Chua S, Chew SL, Yeoh CL, Roy AC, Ho LM, Selamat N, Arulkumaran S, Ratnam SS. A randomized controlled study of prostaglandin 15-methyl F2 alpha compared with syntometrine for prophylactic use in the third stage of labour. Aust N Z J Obstet Gynaecol. 1995 Nov;35(4):413-6. doi: 10.1111/j.1479-828x.1995.tb02155.x. PMID: 8717567.