Dinoprost

HCID 5280363CAS 23518-25-4

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Grundinformationen

Standard-SMILES: CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O
InChIKey: PXGPLTODNUVGFL-YNNPMVKQSA-N
Summenformel: C20H34O5
Durchschnittliche Molmasse: 354,5 g/mol
Monoisotopische Masse: 354,24062418

Namen und Bezeichner

Bevorzugter Name: Dinoprost
IUPAC: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
Englischer Name: (+-)-PGF2-alpha
Summenformel: C20H34O5
Molmasse: 354.48

Namen und Synonyme

dinoprostprostaglandin F2alphaProstaglandin F2aPGF2alphaamoglandinEnzaprostpanacelanProtamodinl-PGF2-alphaPGF2aProstaglandin F2-alphaDinoprosta

Weitere Namen anzeigen

PIGF-2(+-)-PGF2αdl-Prostaglandin F2αProsta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9α,11α,13E,15S)-(±)-(5Z,9α,11α,13E,15S)-(±)-9,11,15-Trihydroxyprosta-5,13-dien-1-oic acid (ACI)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]-, (+-)- (8CI)

DinoprostumProsmonl-Prostaglandin F2-alphaProstarmon FProstin F2alphaProstin F2-alphaPGF-2alphaPGF2-alpha

Datenbank-Bezeichner

CAS: 23518-25-4、551-11-1
PubChem CID: 5280363
DTXSID: DTXSID9022946
ChEMBL: CHEMBL815
ChEBI: CHEBI:15553
UNII: B7IN85G1HY
EC Number: 684-259-0
Nikkaji: J9.246K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 98 Å²
H-Brücken-Donoren: 4
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 12
Schwere Atome: 25
Formalladung: 0
Komplexität: 432

Experimentelle und physikochemische Eigenschaften

Color/FormNATURAL FORM, CRYSTALS

Solubility · 2 Einträge

SOL IN WATER 200 MG/ML /DINOPROST TROMETHAMINE/

FREELY SOL IN METHANOL, ABSOLUTE ETHANOL; FREELY SOL IN ETHYL ACETATE, CHLOROFORM; SLIGHTLY SOL IN WATER

Melting Point25-35 °C

Optical RotationSPECIFIC OPTICAL ROTATION: +23.5 DEG @ 25 °C/D (1 G IN 100 ML TETRAHYDROFURAN)

Stability/Shelf Life · 3 Einträge

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, & HEAT /DINOPROST TROMETHAMINE/

Collision Cross Section · 3 Einträge

191.3 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

207.33 Å² [M+Na]+ [CCS Type: DT; Method: stepped-field]；205.7 Å² [M+Na]+ [CCS Type: DT; Method: stepped-field]；194.77 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

204.4 Å² [M+Na]+；194.1 Å² [M-H]-

Physikochemische Eigenschaften

Siedepunkt: 407.69 °C · 407.69°C (rough estimate)
Dichte: 1.0458 · 1.0458 (rough estimate)
Brechungsindex: 1.612 · 1.6120 (estimate)
storage temp.: -20 °C · -20°C
pka: 4.76 · 4.76±0.10(Predicted)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H319 (89.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H360 (97.4%): May damage fertility or the unborn child [Danger Reproductive toxicity]；H370 (89.7%): Causes damage to organs [Danger Specific target organ toxicity, single exposure]；H372 (89.7%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

P203, P260, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P308+P316, P318, P319, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory InformationDinoprost: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Eye Irrit. 2 (89.7%)；Repr. 1B (97.4%)；STOT SE 1 (89.7%)；STOT RE 1 (89.7%)

Toxikologische Informationen

InteractionsCONTRACTIONS IN RESPONSE TO PROSTAGLANDIN F2ALPHA IN HUMAN ISOLATED BRONCHIAL MUSCLE ARE INHIBITED BY FENAMATES, PHENYLBUTAZONE, &, LESS POTENTLY, ASPIRIN.

Human Toxicity Excerpts · 5 Einträge

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.

Non-Human Toxicity Excerpts · 1 Eintrag

IN PREGNANT RATS TREATED SC @ 50 UG, DAYS 9-11 OR 12-15 OF GESTATION, PLACENTA SHOWED EXTENSIVE AREAS OF DEGENERATION THAT ARE FOUND IN PLACENTAL INSUFFICIENCY. ALSO FETAL ADRENAL CORTEX SHOWED MORPHOLOGICAL CHANGES INDICATIVE OF INTRAUTERINE DISTRESS.

Antidote and Emergency TreatmentSINCE DINOPROST IS METABOLIZED RAPIDLY, DISCONTINUATION OF DRUG & SUPPORTIVE THERAPY ARE ADEQUATE TREATMENT...BLOOD TRANSFUSIONS MAY BE REQUIRED /FOR HEMORRHAGE DUE TO RETENTION OF PLACENTA/

Regulatorische Informationen

Sicherheitsdaten

risk_code: 20-35
hazard_code: C
safety_code: 26-36/37/39-45

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

G - Genito urinary system and sex hormones；G02 - Other gynecologicals；G02A - Uterotonics；G02AD - Prostaglandins；G02AD01 - Dinoprost

QG - Genito urinary system and sex hormones；QG02 - Other gynecologicals；QG02A - Uterotonics；QG02AD - Prostaglandins；QG02AD01 - Dinoprost

Mechanism of Action · 4 Einträge

...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/

Metabolism/Metabolites...PROSTAGLANDINS ARE RAPIDLY METABOLIZED... /PROSTAGLANDINS/

MeSH Pharmacological Classification · 2 Einträge

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)

Absorption, Distribution and Excretion · 3 Einträge

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/

Verwendung und Herstellung

Uses · 2 Einträge

MEDICATION (VET)

MEDICATION

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

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.

General Manufacturing Information · 5 Einträge

...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/