Prostaglandin F2
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Prostaglandin F2
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CAS No:
551-11-1
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Formula:
C20H34O5
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Chemical Name:
Prostaglandin F2
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Synonyms:
Prosta-5,13-dien-1-oic acid,9,11,15-trihydroxy-,(5Z,9α,11α,13E,15S)-;5-Heptenoic acid,7-[3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-;(5Z,9α,11α,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dien-1-oic acid;PGF2α;Prostaglandin F2α;Prostaglandin F2a;Dinoprost;7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid;U 14583;9α,11α,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid;(+)-Prostaglandin F2α;Prostin F 2 alpha;PGF2a;Enzaprost;Amoglandin;Enzaprost F;Prostaglandin F2;Panacelan;Cyclosin;Prostarmon F;9α,11α-PGF2;Protamodin;Cyclosin (pharmaceutical);Glandin N;9α,11α-PGF2α;Dinifertin;Prostamate;Croniben;Glandin;99437-94-2;13535-33-6
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Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System
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CAS No:
Description
Dinoprost(Prostaglandin F2α) is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.
Prostaglandin F2alpha is a prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor. It has a role as a human metabolite and a mouse metabolite. It is a prostaglandins Falpha and a monocarboxylic acid. It is a conjugate acid of a prostaglandin F2alpha(1-).|Dinoprost has been investigated in Headache.|Dinoprost is a synthetic analogue of the naturally occurring prostaglandin F2 alpha. Prostaglandin F2 alpha stimulates myometrial activity, relaxes the cervix, inhibits corpus luteal steroidogenesis, and induces luteolysis by direct action on the corpus luteum. (NCI04)|A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.
Prostaglandin F2 Basic Attributes
354.48
354.48
B7IN85G1HY
DTXSID9022946
C65413
NATURAL FORM, CRYSTALS
G - Genito urinary system and sex hormones
Characteristics
97.99000
2.14
White to off-white crystalline solid.
1.2±0.1 g/cm3
25-35 °C
531.0±50.0 °C at 760 mmHg
289.0±26.6 °C
1.569
FREELY SOL IN METHANOL, ABSOLUTE ETHANOL; FREELY SOL IN ETHYL ACETATE, CHLOROFORM; SLIGHTLY SOL IN WATER
Store in a tightly closed container.
LD50 in rabbits (mg/kg): 2.5-5.0 i.v.; 2.5-5.0 i.m. (Fujita)
D25 +23.5° (c = 1 in tetrahydrofuran)
205.7 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|207.33 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|194.77 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|194.1 Ų [M-H]-
ODORLESS, BITTER-TASTING /DINOPROST TROMETHAMINE/|MP APPROX 100 °C /DINOPROST TROMETHAMINE/|WHITE OR OFF-WHITE CRYSTALLINE POWDER /DINOPROST TROMETHAMINE/
Safety Information
I
1.1A
224
S28
STABLE IN LIGHT, AIR, & HEAT /DINOPROST TROMETHAMINE/
P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
H302
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P280, P281, P301+P312, P305+P351+P338, P307+P311, P308+P313, P314, P321, P330, P337+P313, P405, and P501|Aggregated GHS information provided by 38 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
CONTRACTIONS IN RESPONSE TO PROSTAGLANDIN F2ALPHA IN HUMAN ISOLATED BRONCHIAL MUSCLE ARE INHIBITED BY FENAMATES, PHENYLBUTAZONE, &, LESS POTENTLY, ASPIRIN.
Drug Information
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/|For more Therapeutic Uses (Complete) data for PROSTAGLANDIN F2ALPHA (15 total), please visit the HSDB record page.
ASTHMATIC INDIVIDUALS ARE PARTICULARLY SENSITIVE, & PGF2ALPHA HAS CAUSED INTENSE BRONCHOSPASM.|SOME INVESTIGATORS HAVE INDICATED THAT PROSTAGLANDINS MAY SHOW NARROWER DOSE-RESPONSE RANGE FOR PRODN OF PHYSIOLOGICAL CONTRACTIONS & OCCURRENCE OF UTERINE HYPERTONUS, POTENTIAL HAZARD THAT MAY BE AVOIDED BY VERY CAUTIOUS STEPWISE INCREMENTS IN RATE OF INFUSION. /PROSTAGLANDINS/|FOR ABORTION IN 2ND TRIMESTER...RESULTS IN...FREQUENT BUT TOLERABLE SIDE EFFECTS. HOWEVER, FOR VERY EARLY ABORTION (MENSES DELAYED UP TO SEVERAL WK), RATE OF SUCCESS REPORTED IS LOW & SERIOUS SIDE EFFECTS HAVE RESULTED FROM DOSES REQUIRED. /PROSTAGLANDINS/|...CONTRAINDICATED IN ACUTE PELVIC INFLAMMATION. IT SHOULD BE USED CAUTIOUSLY IN PT WITH HISTORY OF HYPERTENSION, ASTHMA, GLAUCOMA, EPILEPSY, OR CARDIOVASCULAR DISEASE.|For more Drug Warnings (Complete) data for PROSTAGLANDIN F2ALPHA (11 total), please visit the HSDB record page.
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) (See all compounds classified as Oxytocics.)|Non-steroidal chemical compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Nonsteroidal.)
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/
...PROSTAGLANDINS ARE RAPIDLY METABOLIZED... /PROSTAGLANDINS/
...THERE IS NO SINGLE PROSTAGLANDIN RECEPTOR. ... IT IS POSSIBLE TO DEMONSTRATE CALCIUM DEPENDENCE OF DIVERSE RESPONSES TO PROSTAGLANDINS & TO OBSERVE ALTERED CALCIUM FLUXES. ...PROSTAGLANDINS MAY EITHER STIMULATE OR INHIBIT ACCUM OF CYCLIC AMP. /PROSTAGLANDINS/|RESPONSES TO PROSTAGLANDIN F2ALPHA SHOW SPECIES VARIATION, BUT VASODILATATION HAS BEEN OBSERVED FOLLOWING INJECTION INTO HUMAN BRACHIAL ARTERY OF PGF2ALPHA... SUPERFICIAL VEINS OF HAND ARE CONTRACTED BY PFG2ALPHA...|PROMPT SUBSIDENCE OF PROGESTERONE OUTPUT & REGRESSION OF CORPUS LUTEUM FOLLOWS PARENTERAL INJECTION OF PROSTAGLANDIN F2ALPHA... THIS EFFECT INTERRUPTS EARLY PREGNANCY, WHICH IS DEPENDENT ON LUTEAL RATHER THAN PLACENTAL PROGESTERONE.|OXYTOCIN & PROSTAGLANDINS AFFECT UTERINE SMOOTH MUSCLES BY DIFFERENT MECHANISMS, & THEIR EFFECTS ARE ADDITIVE. POSSIBLE ADVANTAGES OF THEIR COMBINED USE ARE BEING EXPLORED. /PROSTAGLANDINS/
SINCE DINOPROST IS METABOLIZED RAPIDLY, DISCONTINUATION OF DRUG & SUPPORTIVE THERAPY ARE ADEQUATE TREATMENT...BLOOD TRANSFUSIONS MAY BE REQUIRED /FOR HEMORRHAGE DUE TO RETENTION OF PLACENTA/
INTRADERMAL INJECTION OF.../PROSTAGLANDIN F2ALPHA/ IN MAN CAUSES "WHEAL & FLARE."|SIDE EFFECTS ATTENDING USE OF PROSTAGLANDINS IN SECOND & THIRD TRIMESTER & @ TERM ARE CAUSED BY THEIR STIMULATORY ACTION ON SMOOTH MUSCLE OF ALIMENTARY TRACT, THAT IS, NAUSEA, VOMITING, & DIARRHEA. /PROSTAGLANDINS/|CERVICAL OR LOWER UTERINE LACERATION OR RUPTURE, WITH RETENTION OF PLACENTA & HEMORRHAGE, IS PERHAPS MOST IMPORTANT DANGER WITH USE...FOR 2ND-TRIMESTER ABORTION. ... FEVER, HYPOTENSION & SYNCOPE, HYPERTENSION, HEADACHE, & PAIN & ERYTHEMA @ SITE OF INJECTION OCCUR LESS FREQUENTLY. /DINOPROST TROMETHAMINE/|BRONCHOSPASM...IN...ASTHMATIC PT; GRAND MAL CONVULSIONS...OCCUR...IN PT PRONE TO EPILEPSY. VASOMOTOR REACTIONS, ARRHYTHMIAS, ATRIOVENTRICULAR CONDUCTION DISTURBANCES, HYPERVENTILATION, PARESTHESIAS & HYPERESTHESIAS, CHEST PAIN, HICCUPS, & DYSURIA HAVE BEEN OBSERVED AFTER INTRAUTERINE ADMIN... /DINOPROST TROMETHAMINE/|For more Human Toxicity Excerpts (Complete) data for PROSTAGLANDIN F2ALPHA (6 total), please visit the HSDB record page.
9alpha,11beta PGF2
Prostaglandin F2 Use and Manufacturing
...SYNTH OF NATURAL PROSTAGLANDIN F2ALPHA: SCHNEIDER, MURRAY, J ORG CHEM 38, 397 (1973).
Prostanoid receptor ligand
...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.
...20-CARBON UNSATURATED CARBOXYLIC ACIDS WITH CYCLOPENTANE RING. ...KINSHIP WITH ESSENTIAL FATTY ACIDS... MAIN CLASSES--E, F, A, B, C, & D-DISTINGUISHED BY CONSTITUENTS OF...RING. ...SUBDIVIDED...WITH NUMBER OF DOUBLE BONDS IN SIDE CHAINS. ...INDICATED BY SUBSCRIPT...REFLECTS FATTY ACID PRECURSOR. /PROSTAGLANDINS/|PROSTAGLANDINS OF E & FALPHA SERIES ARE SOMETIMES REFERRED TO AS "PRIMARY PROSTAGLANDINS". ...MOST ABUNDANT (ESP E2 & F2ALPHA)... /PROSTAGLANDINS/|IN VIVO MOST CELLS SEEM CAPABLE OF SYNTHESIZING PROSTAGLANDINS FROM ESSENTIAL FATTY ACID PRECURSORS. ...BELIEVED THAT ENDOGENOUS BIOSYNTHESIS, IN ABSENCE OF ADDED PRECURSOR ACID, DEPENDS ON PHOSPHOLIPASE-CATALYZED RELEASE OF PRECURSOR ACID FROM CELLULAR PHOSPHOLIPID STORES. /PROSTAGLANDINS/|SYNTH OF PRIMARY PROSTAGLANDINS...BY COMPLEX OF MICROSOMAL ENZYMES REFERRED TO AS "PROSTAGLANDIN SYNTHETASE." INITIAL EVENTS...RESULT IN OXYGENATION & CYCLIZATION OF UNESTERIFIED PRECURSOR ACID TO FORM CYCLIC PEROXIDE DERIV. ...ENDOPEROXIDE IS...REDUCED, YIELDING PGFALPHA COMPD. /PROSTAGLANDINS/|MOST PROLIFIC SOURCE OF NATURAL PROSTAGLANDINS IS MARINE ORGANISM CALLED GORGONIAN SEA WHIP, WHICH OCCURS...IN CORAL REEFS, ESP IN CARIBBEAN AREA. HARVESTING OF THESE HAS MADE PRODN...MUCH LESS EXPENSIVE. INTERMEDIATES & CHEM ANALOGS DERIVED FROM THIS NATURAL SOURCE...SYNTONS. /PROSTAGLANDINS/
RADIOIMMUNOASSAY OF PROSTAGLANDIN (DINOPROST) F2ALPHA IS DISCUSSED.
Fatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Computed Properties
Molecular Weight:354.5
XLogP3:2.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:12
Exact Mass:354.24062418
Monoisotopic Mass:354.24062418
Topological Polar Surface Area:98
Heavy Atom Count:25
Complexity:432
Defined Atom Stereocenter Count:5
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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