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Your Location：Home>Product Center >> Pharmaceutical API >> Prostaglandin F2α
  • Prostaglandin F2α
Name:Prostaglandin F2α
CAS No:551-11-1

PRODUCT DESCRIPTION

【Name】
Prosta-5,13-dien-1-oicacid, 9,11,15-trihydroxy-, (5Z,9a,11a,13E,15S)-
【CAS Registry number】
551-11-1
【Synonyms】
(+)-ProstaglandinF2a
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid
9a,11a-PGF2
9a,11a-PGF2a
Amoglandin
Cyclosin
Cyclosin (pharmaceutical)
Dinifertin
Dinoprost
Enzaprost
Enzaprost F
Glandin N
PGF2a
Panacelan
Prostaglandin F2
Prostaglandin F2a
Prostamate
Prostarmon F
Prostin F 2 alpha
Protamodin
U 14583
【Molecular Formula】
C20H34O5 (Products with the same molecular formula)
【Molecular Weight】
354.48096
【Inchi】
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
【InChIKey】
PXGPLTODNUVGFL-YNNPMVKQSA-N
【Canonical SMILES】
CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
【Isomers smiles】
CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=CCCCC(=O)O)O)O)O
【MOL File】

Chemical and Physical Properties

【Appearance】
White to off-white crystalline solid.
【Density】
1.153 g/cm3
【Melting Point】
25–35ºC
【Boiling Point】
531 °C at 760 mmHg
【Refractive Index】
1.569
【Flash Point】
289 °C
【Water】
100mg/ml soluble in 100% ethanol, DMSO or dimethyl formamide; also soluble in aqueous buffers (10mg/ml in PBS, pH 7.2).
【Solubilities】
100mg/ml soluble in 100% ethanol, DMSO or dimethyl formamide; also soluble in aqueous buffers (10mg/ml in PBS, pH 7.2).
【Color/Form】
NATURAL FORM, CRYSTALS
【Stability】
Stable for 2 yr in light resistant containers @ 5-15 C degrades in 1 wk when exposed to sunlight or in 3 mo @ 40 C stable in light, air, and heat.
【Storage temp】
Store in a tightly closed container.
【Spectral properties】
SPECIFIC OPTICAL ROTATION: +23.5 DEG @ 25 DEG C/D (1 G IN 100 ML TETRAHYDROFURAN)
【Computed Properties】
Molecular Weight:354.48096 [g/mol]
Molecular Formula:C20H34O5
XLogP3:2.7
H-Bond Donor:4
H-Bond Acceptor:5
Rotatable Bond Count:12
Exact Mass:354.240624
MonoIsotopic Mass:354.240624
Topological Polar Surface Area:98
Heavy Atom Count:25
Formal Charge:0
Complexity:432
Isotope Atom Count:0
Defined Atom Stereocenter Count:5
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:2
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:3
Feature 3D Anion Count:1
Feature 3D Hydrophobe Count:3
Feature 3D Ring Count:1
Effective Rotor Count:13
Conformer Sampling RMSD:1.2
CID Conformer Count:127

Safety and Handling

【Safety】
Poison by subcutaneous, intravenous, and intramuscular routes. Moderately toxic by ingestion. Human and experimental teratogenic and experimental reproductive effects. Human reproductive effects by subcutaneous, intravenous, intramuscular, intraperitoneal, intravaginal, and intraplacental routes: postpartum depression and other maternal effects, abortion, and changes in measures of fertility. Human teratogenic effects by intraplacental route: extra embryonic structures. Human systemic effects by intravenous route: hypermotility, diarrhea, nausea or vomiting. Human mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
【Formulations/Preparations】
...SOLN CONTAINING EQUIV OF 5 MG OF PROSTAGLANDIN F2ALPHA PER MILLILITER; IT IS AVAIL IN 4- & 8-ML AMPULS FOR INTRA-AMNIOTIC ADMIN TO INDUCE ABORTION.
【Specification】

usageEng: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

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

...SYNTH OF NATURAL PROSTAGLANDIN F2ALPHA: SCHNEIDER, MURRAY, J ORG CHEM 38, 397 (1973).
【Usage】
Medication (vet).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Non-steroidal chemical compounds with abortifacient activity.
- Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157)
【Therapeutic Uses】
Abortifacient Agents, Nonsteroidal; Oxytocics
...SOME PHYSICIANS PREFER TO DEFER ABORTION UNTIL AFTER 16TH WK, WHEN INTRA-AMNIOTIC ROUTE CAN BE EMPLOYED MORE SAFELY. /DINOPROST TROMETHAMINE/
EXTRA-AMNIOTIC TECHNIQUE, WHICH IS STILL INVESTIGATIONAL, REQUIRES TRANSVAGINAL INTRAUTERINE EXTRAOVULAR PLACEMENT OF INDWELLING CATHETER. ... RESERVED FOR TERMINATION OF PREGNANCIES BETWEEN 13TH & 15TH WK... /DINOPROST TROMETHAMINE/
DOSAGE THAT ACHIEVES EFFECTIVE CONCN WITHIN MYOMETRIUM IS LOWEST WITH INTRAUTERINE ADMIN. INTRA-AMNIOTIC INSTILLATION IS ACCOMPLISHED WITH LONG SPINAL NEEDLE INSERTED TRANSABDOMINALLY INTO AMNIOTIC SAC. /DINOPROST TROMETHAMINE/
...MOST SATISFACTORY RESULTS WERE OBTAINED WITH INTRA-AMNIOTIC INSTILLATION OF 40 MG OF PGF(2ALPHA), FOLLOWED BY ADDITIONAL 20 MG 6 HR LATER. ...COMPLETE ABORTION WAS OBTAINED IN OVER 80% OF 70 PT...MOST PT ABORTED WITHIN 24 & ALL WITHIN 48 HR.
...INDICATED THEIR USEFULNESS IN TREATING MISSED ABORTION, LATE INTRAUTERINE DEATH, MOLAR GESTATION, & PREMATURE RUPTURE OF MEMBRANES. /PROSTAGLANDINS/
BECAUSE INDIVIDUAL RESPONSES TO...PGF(2ALPHA)...ARE HIGHLY VARIABLE & INVOLVE LAG PERIOD...INDUCTION OF LABOR...SHOULD BE CARRIED OUT BY STEPWISE INCREMENTS OF IV INFUSION OF DILUTE SOLN. ...OVER PERIOD OF 10 HR.
ALTHOUGH RESPONSE OF UTERUS TO PROSTAGLANDINS...INCR AS GESTATION PROGRESSES, THESE AGENTS ARE MUCH MORE EFFECTIVE...IN EARLIER MO. FOR ABORTION IN 2ND TRIMESTER, INTRAUTERINE INSTILLATION...CERVICAL CATHETER OR INTRA-AMNIOTIC INJECTION OF...PGF(2ALPHA) RESULTS IN HIGH SUCCESS RATE...
...POTENTIAL USES RELATED TO REPRODUCTIVE SYSTEM MIGHT INCL DYSMENORRHEA, PREMATURE LABOR, OR FERTILITY CONTROL. ...CAN BE CONSIDERED TO BE LOCAL HORMONES SINCE...THEY EXERT THEIR EFFECTS & ARE INACTIVATED...IN TISSUES OR ORGANS IN WHICH THEY ARE SYNTHESIZED. /PROSTAGLANDINS/
...HUMAN UTERUS...ALWAYS CONTRACTED... RESPONSE IS PROMPT & DOSE DEPENDENT... SHARP RISE IN TONUS WITH SUPERIMPOSED RHYTHMIC CONTRACTIONS, WHICH LONG OUTLAST TONIC PHASE. IV INFUSION RESULTS IN SUSTAINED LABOR-LIKE CONTRACTIONS WITH TONE FALLING BETWEEN EACH. ...SENSITIVITY DOES INCR @ TERM. /PROSTAGLANDINS/
INTRA-AMNIOTIC INSTILLATION: SPINAL NEEDLE (NUMBER 18-22) IS USED FOR TRANSABDOMINAL INTRA-AMNIOTIC TAP. 1 OR MORE ML OF FLUID IS REMOVED, & 40 MG...IS INJECTED SLOWLY... /DINOPROST TROMETHAMINE/
NAUSEA & VOMITING, WHICH OCCUR IN @ LEAST 50% OF PT, IS AMELIORATED OR PREVENTED BY PARENTERAL ADMIN OF ANTIEMETICS. /DINOPROST TROMETHAMINE/
MEDICATION (VET): IT HAS BEEN SUGGESTED AS "MORNING AFTER" CONTRACEPTIVE.
SERIES OF 50 HIGH RISK PREGNANCY PT @ 35-42 WK GESTATION WERE INDUCED WITH IV PROSTAGLANDIN F2ALPHA ADMIN @ RATE OF 0.5 MCG/MIN & INCR HOURLY UNTIL EITHER THE UTERUS WAS CONTRACTING REGULARLY OR PROGRESS WAS OCCURRING. GI SIDE EFFECTS OCCURRED IN 24% OF PT.
ESTRUS WAS INDUCED IN 30 OF 31 COWS TREATED. OVULATION WAS OBSERVED IN 2 ANIMALS ON 3RD DAY, IN 23 ANIMALS ON 4TH DAY & IN 6 ANIMALS ON 5TH DAY OF TREATMENT. FERTILITY WAS 83.9%.
【Biomedical Effects and Toxicity】
AMONG COMPD OCCURRING IN SEMEN THAT ARE OF CURRENT RESEARCH INTEREST ARE PROSTAGLANDINS (25 MG/ML). /PROSTAGLANDINS/
APART FROM GENERALLY SLOW & SPECIES-DEPENDENT ISOMERIZATION, PGS E & F ARE RATHER STABLE IN BLOOD, BUT THEY ARE RAPIDLY DEGRADED & INACTIVATED BY TISSUE-BOUND ENZYMES; SOME 80-90% OR MORE IS DESTROYED DURING SINGLE PASSAGE THROUGH LIVER OR LUNGS. /PROSTAGLANDINS/
DEG OF BINDING OF PROSTAGLANDINS TO PLASMA PROTEINS APPEARS TO HAVE LITTLE INFLUENCE ON THEIR RATES OF METABOLISM & ELIMINATION. ... CLEARANCE RATES OF (3)H DID NOT CHANGE WHETHER PROSTAGLANDINS WERE ADMIN IN FREE FORM OR BOUND TO RAT PLASMA ALBUMIN. /PROSTAGLANDINS/

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