Carboprost (15(S)-15-Methyl Prostaglandin F2α) is a metabolically stable synthetic analog of prostaglandin F2α. Carboprost stimulates uterine contractions and causes miscarriage. Carboprost is used for postpartum hemorrhage due to uterine atony and for termination of pregnancy in the second trimester.

Physicochemical Properties

Molecular Formula	C21H36O5
Molecular Weight	368.50754
Exact Mass	368.256
CAS #	35700-23-3
PubChem CID	5281075
Appearance	White to off-white ointment
Density	1.1±0.1 g/cm3
Boiling Point	536.6±50.0 °C at 760 mmHg
Melting Point	79-82ºC
Flash Point	292.4±26.6 °C
Vapour Pressure	0.0±3.2 mmHg at 25°C
Index of Refraction	1.565
LogP	2.49
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	12
Heavy Atom Count	26
Complexity	473
Defined Atom Stereocenter Count	5
SMILES	CCCCC[C@@](C)(/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@H](C[C@H]1O)O)O
InChi Key	DLJKPYFALUEJCK-IIELGFQLSA-N
InChi Code	InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
Chemical Name	(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vivo	Serum progesterone was lowered to 12% of pretreatment values within 24 hours of administering carboprost methyl ester (15(S)-15-methylprostaglandin F2α; 15M-PGF2α, 12.5 mg/monkey); however, progesterone returned to normal range within 48 hours. [1].
References	[1]. Effect of Intramuscular 15-methyl Prostaglandin F2 Alpha After Second-Trimester Delivery. Obstet Gynecol. 1997 Jan;89(1):5-9. [2]. Inhibition of the Monkey Corpus Luteum With 15-methyl Prostaglandins. Prostaglandins. 1980 Nov;20(5):793-805.
Additional Infomation	Carboprost is prostaglandin F2alpha in which the hydrogen at position 15 is substituted by methyl (S configuration). It is used as an abortifacient agent that is effective in both the first and second trimesters of pregnancy. It has a role as an oxytocic and an abortifacient. It is functionally related to a prostaglandin F2alpha. It is a conjugate acid of a carboprost(1-). Carboprost is a Prostaglandin Analog. Carboprost is the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 alpha (PGF2 alpha) with oxytocic activity. Mimicking endogenous PGF2 alpha, carboprost activates prostaglandin F receptor, a G-protein coupled receptor, on smooth muscle cells, thereby resulting in smooth muscle contractions. When administered intramuscularly on gravid subjects, this agent induces myometrium contractions, thereby initiating luteolysis and consequently parturition. Furthermore, carboprost's action on vascular smooth muscle and gastrointestinal tract sphincters leads to raised blood pressure and induces vomiting or diarrhea, respectively. A nonsteroidal abortifacient agent that is effective in both the first and second trimesters of PREGNANCY. See also: Carboprost Tromethamine (has salt form).

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~271.36 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.78 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.78 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.7136 mL	13.5682 mL	27.1363 mL
	5 mM	0.5427 mL	2.7136 mL	5.4273 mL
	10 mM	0.2714 mL	1.3568 mL	2.7136 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.