(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid; 2-amino-2-(hydroxymethyl)propane-1,3-diol

• ChemBase ID: 1031
• Molecular Formular: C24H45NO8
• Molecular Mass: 475.616
• Monoisotopic Mass: 475.31451741
• SMILES: O[C@@H]1[C@@H]([C@H]([C@H](O)C1)/C=C/[C@@H](O)CCCCC)C/C=C\CCCC(=O)O.OCC(N)(CO)CO
• Canonical SMILES: OCC(CO)(CO)N.CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
• InChI: InChI=1S/C20H34O5.C4H11NO3/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1
• InChIKey: IYGXEHDCSOYNKY-RZHHZEQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid; 2-amino-2-(hydroxymethyl)propane-1,3-diol
• IUPAC Traditional name: glandin; tris buffer
• Brand Name: Dinolytic; Ensaprost; Lutalyse; Panacelan F tromethamine salt; Pronalgon F; Prostalmon F; Zinoprost
• Synonyms: Dinoprost, trometamol salt; PGF2-alpha THAM; PGF2alpha THAM; Prostaglandin F2-alpha THAM; Prostaglandin F2a tromethamine; Prostaglandin F2alpha tham; Prostin F2 Alpha; Dinoprost Tromethamine; (5Z,9α,11α,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dien-1-oic Acid 2-Amino-2-(hydroxymethyl)-1,3-propanediol; 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic Acid Tromethamine; (+)-Prostaglandin F2α Tromethamine; 9α,11α,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic Acid Tromethamine; 9α,11α-PGF2 Tromethamine; 9α,11α-PGF2α Tromethamine; Prostaglandin F2α-tham; THAM PGF2α; Tromethamine Prostaglandin F2α; U 14583E; U 14585; Prostaglandin F2α Tromethamine Salt

Database IDs

• CAS Number: 38562-01-5
• PubChem SID: 160964494; 46509164
• PubChem CID: 5282415

CALCULATED PROPERTIES

• Acid pKa: 4.355294
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4380769
• LogD (pH = 7.4): -0.31100234
• Log P: 2.6110544
• Molar Refractivity: 100.4707 cm^3
• Polarizability: 38.732555 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.2 g/mL; Methanol; THF
• Apperance: White Solid
• Melting Point: 100-103°C
• Hydrophobicity(logP): -0.12

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB01160

• Drug Groups: approved
• Description: The tromethamine (THAM) salt of the naturally occurring prostaglandin F2 alpha, dinoprost tromethamine occurs as a white to off-white, very hygroscopic, crystalline powder. Dinoprost tromethamine may also be known as dinoprost trometamol, PGF2 alpha THAM, or prostaglandin F2 alpha tromethamine.
• Indication: Used for aborting second-trimester pregnancy (between the twelfth to eighteenth week of gestation) and in incomplete abortion or for therapeutic abortion in cases of intrauterine fetal death and congenital abnormalities incompatible with life. Also used at low-doses for medically indicated induction of labor at term. Also injected intra-arterially for use as a vasodilator to assist in angiography.
• Pharmacology: Dinoprost tromethamine is the tromethamine (THAM) salt of the naturally occurring prostaglandin F2_alpha. Prostaglandin F2_alpha has several pharmacologic effects on the female reproductive system, including stimulation of myometrial activity, relaxation of the cervix, inhibition of steroidogenesis by corpora lutea, and can potentially lyse corpora lutea.
• Toxicity: Although overdose by intra-amniotic administration of dinoprost has not been reported, exaggeration of the nausea, vomiting, and diarrhea that occur with normal doses would be expected.
• Affected Organisms: Humans and other mammals
• Biotransformation: Enzymatic dehydrogenation primarily in the maternal lungs and also in the liver.
• Absorption: Slowly absorbed from the amniotic fluid into systemic circulation.
• Half Life: The half-life of dinoprost in amniotic fluid is 3 to 6 hours. The plasma half-life of dinoprost after intravenous administration is reported to be less than 1 minute.

Toronto Research Chemicals - P838625

One of the most biologically studied of the primary prostaglandins. Closely related to Prostaglandin E2 (PGE2) in that both prostaglandins are biosynthesized from the same precursors and that PGF2 is the synthetic reduction product of PGE2. Phospholipase

REFERENCES

• Granstrom, S., et al.: J. Biol. Chem., 246, 5254 (1971)
• Kubota, Y., et al.: Eur. J. Pharmacol., 467, 191 (1971)
• Crowell, J., et al.: Toxicol. Sci., 82, 614 (20040,