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Name:	Prostaglandin F2a tris salt
CAS No:	38562-01-5

PRODUCT DESCRIPTION

【Name】: Prostaglandin F2a tris salt

【CAS Registry number】: 38562-01-5

【Synonyms】: 2-amino-2-(hydroxymethyl)propane-1,3-diol
(E)-7-[(1R,2S,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
Panacelan F tromethamine salt
Enzaprost F compd. with trisamine
Dinoprost tromethamine (JAN/USP)
Prostaglandin F2.alpha., compd. with 2-amino-2-hydroxymethyl-1,3-propanediol (1:1)
Dinoprost tromethamine
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid, tromethamine salt
Prosta-5,13-dien-1-oic acid, (5Z,9.alpha.,11.alpha.,13E,15S)-9,11,15-trihydroxy- compd. with (trimethylolamino)methane
Prosta-5,13-dien-1-oic acid, 9,11, 15-trihydroxy-, (5Z,9.alpha.,11.alpha.,13E,15S)-, compd. with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)
Ensaprost
Pronalgon F
Prosta-5,13-dien-1-oic acid,9,11,15-trihydroxy-,(5Z,9R,11R,13E,- 15S)-,compd. with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)
Zinoprost
Dinoprost Trometamol

【EINECS(EC#)】: 254-002-3

【Molecular Formula】: C₂₀H₃₄O₅^.C₄H₁₁NO₃ (Products with the same molecular formula)

【Molecular Weight】: 475.616

【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

【Canonical SMILES】: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O.C(C(CO)(CO)N)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.C(C
(CO)(CO)N)O

【MOL File】
38562-01-5.mol

Chemical and Physical Properties

【Melting Point】: 25-35 DEG C

【Boiling Point】: 531 °C at 760 mmHg

【Flash Point】: 289 °C

【Water】: H2O: 1 mg/mL Aqueous solutions are stable for 30 days at 2-8°C and for several months frozen at ?0°C in single use aliquots. Avoid repeated freeze/thaw cycles.

【Solubilities】: H2O: 1 mg/mL Aqueous solutions are stable for 30 days at 2-8°C and for several months frozen at ?0°C in single use aliquots. Avoid repeated freeze/thaw cycles.

【Color/Form】: white

【Storage temp】: −20°C

【Spectral properties】: SPECIFIC OPTICAL ROTATION: +23.5 DEG @ 25 DEG C/D (1 G IN 100 ML TETRAHYDROFURAN)

【Computed Properties】: Molecular Weight:475.616 [g/mol]
Molecular Formula:C₂₄H₄₅NO₈
H-Bond Donor:8
H-Bond Acceptor:9
Rotatable Bond Count:15
Exact Mass:475.314517
MonoIsotopic Mass:475.314517
Topological Polar Surface Area:185
Heavy Atom Count:33
Formal Charge:0
Complexity:486
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:2

Safety and Handling

【Hazard Codes】: T: Toxic;

【Risk Statements】: R60;R22

【Safety Statements 】: 53-45

【Safety】

Poison by intraperitoneal, subcutaneous, intravenous, and intramuscular routes. Moderately toxic by ingestion. Human reproductive effects by intervaginal route: terminates pregnancy, effects on fertility. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NO_x. See also PROSTAGLANDIN A1; PROSTAGLANDIN D2; PROSTAGLANDIN E1; PROSTAGLANDIN E2 SODIUM SALT; PROSTAGLANDIN F1-α; PROSTAGLANDIN F2-α; dl-PROSTAGLANDIN F2-α.

Hazard Codes of Prostaglandin F2a tris salt (CAS NO.38562-01-5): Toxic T
Risk Statements:
R22:Harmful if swallowed.
R60:May impair fertility.
Safety Statements:
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S53:Avoid exposure - obtain special instructions before use.

【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】: Prostaglandin F2a tris salt ,its cas register number is 38562-01-5. It also can be called Dinoprost tromethamine ; Dinoprost trometamol ; Dinoprost compd. with 2-amino-2- (hydroxymethyl)-1,3-propanediol (1:1) ; Prostin F2 alpha and Lutalyse .

Use and Manufacturing

【Use and Manufacturing】: Methods of Manufacturing

...SYNTH OF NATURAL PROSTAGLANDIN F2ALPHA: SCHNEIDER, MURRAY, J ORG CHEM 38, 397 (1973).

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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