15(S)-15-methyl Prostaglandin F methyl ester

Cayman Chemical Item Number 16744

15(S)-15-methyl PGF methyl ester; Methyl carboprost; U-36384 (CAS 35700-21-1)

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Description

15(S)-15-methyl PGF methyl ester is a derivative of 15(S)-15-methyl PGF with increased membrane permeability.1,2 Hydrolysis of the methyl ester in vivo releases the biologically active 15(S)-15-methyl PGF, which is a potent uterine stimulant and abortifacient.3,4,5

1. Roseman, T.J., Biermacher, J.J., Bennett, R.M., et al. Design criteria for controlled release delivery systems of carboprost methyl. J Control Release 3 25-37 (1986).

2. Halstead, G.W., and Theis, D.L. Drug release testing of a prostaglandin containing controlled-release vaginal device: Development of a semi-automated method. J Pharm Sci 74 1086-1090 (1985).

3. Carlan, S.J., Gushwa, J.P., O'Brien, W.F., et al. Effect of intramuscular 15-methyl prostaglandin F after second-trimester delivery. Obstet Gynecol 89 5-9 (1997).

4. Lindblom, B., Källfelt, B., Hahlin, M., et al. Local prostaglandin F injection for termination of ectopic pregnancy. Lancet 776-777 (1987).

5. Adaikan, P.G., Prasad, R.N.V., Kottegoda, S.R., et al. Effect of indomethacin on the injection-abortion interval of 15(S)15 methyl PGF-induced mid-trimester abortions - a randomized study. Prostaglandins Leukot Med 27 161-167 (1987).

Synonyms
  • 15(S)-15-methyl PGF methyl ester
  • Methyl carboprost
  • U-36384
Formal Name 9α,​11α,​15S-​trihydroxy-​15-​methyl-​prosta-​5Z,​13E-​dien-​1-​oic acid,​ methyl ester
CAS Number 35700-21-1
Molecular Formula C22H38O5
Formula Weight 382.5
Formulation A crystalline solid
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1[C@H]​(C/C=C\CCCC(OC)​=O)​[C@@H]​(/C=C/[C@@]​(C)​(O)​CCCCC)​[C@H]​(O)​C1
InCHI Code
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​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
InCHI Key
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QQCOAAFKJZXJFP-XAYIDPIISA-N

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15(S)-15-methyl Prostaglandin F methyl ester is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $42.00 $0.00
5 mg $189.00 $0.00
10 mg $336.00 $0.00
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15(S)-15-methyl Prostaglandin F
Prostaglandin F

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