Vasopressin(CAS No. 11000-17-2)

Vasopressin C46H65N13O12S2 (cas 11000-17-2) Molecular Structure

11000-17-2 Structure

Identification and Related Records

【Name】
Vasopressin
【Iupac name】
(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[
(4R,7S,10S,13S,16S,
19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-
16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,
17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;
(2S)-1-[(4R,7S,10S,13S,16S,
19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-
16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,
17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]
-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
【CAS Registry number】
11000-17-2
【Synonyms】
ADH (hormone)
Antidiuretic hormone
Inyectable de vasopresina
Leiormone
3-(Phenylalanine)-8-lysine oxytocin
Vasopressin injection
beta-Hypophamine
Vasopressinum
Pitressin
Pituitrin
【EINECS(EC#)】
200-050-5
【Molecular Formula】
C46H65N13O12S2 (Products with the same molecular formula)
【Molecular Weight】
2140.48
【Inchi】
InChI=1/C46H65N15O12S2.C46H65N13O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25;47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53);1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69)
【Canonical SMILES】
C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)NC(CCCCN)C(=O)NCC(=O)N.C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N
【MOL File】
11000-17-2.mol

Chemical and Physical Properties

【Density】
g/cm3
【Boiling Point】
°Cat760mmHg
【Flash Point】
°C
【Solubilities】
WATER SOLUBLE
【Color/Form】
CLEAR COLORLESS OR PRACTICALLY COLORLESS LIQUID
【Computed Properties】
Molecular Weight:2140.4498 [g/mol]
Molecular Formula:C92H130N28O24S4
H-Bond Donor:27
H-Bond Acceptor:32
Rotatable Bond Count:38
Tautomer Count:1001
Exact Mass:2138.86956
MonoIsotopic Mass:2138.86956
Topological Polar Surface Area:991
Heavy Atom Count:148
Formal Charge:0
Complexity:4030
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:16
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Formulations/Preparations】
ARGININE VASOPRESSIN...ARGIPRESSIN, RINDER-VASOPRESSIN.
ARGININE VASOPRESSIN, C46H65N15O12S2, ARGIPRESSIN RINDERVASOPRESSIN.
VASOPRESSIN TANNATE (PITRESSIN TANNATE) IS WATER-INSOL TANNATE OF ANTIDIURETIC PRINCIPLE. IT IS MARKETED SUSPENDED IN PEANUT OIL (VASOPRESSIN TANNATE INJECTION). EACH ML CONTAINS 5 PRESSOR UNITS.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

...BY SYNTHESIS OR OBTAINED FROM POSTERIOR LOBE OF PITUITARY OF HEALTHY DOMESTIC ANIMALS USED FOR FOOD BY MAN: USP XVII, 770. ... PURIFICATION: TURNER ET AL, J BIOL CHEM 191, 21 (1951).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that reduce the excretion of URINE, most notably the octapeptide VASOPRESSINS.
- Agents acting to arrest the flow of blood. Absorbable hemostatics arrest bleeding either by the formation of an artificial clot or by providing a mechanical matrix that facilitates clotting when applied directly to the bleeding surface. These agents function more at the capillary level and are not effective at stemming arterial or venous bleeding under any significant intravascular pressure.
- Drugs used to cause constriction of the blood vessels.
【Therapeutic Uses】
ADH PROVIDES MOST EFFECTIVE THERAPY FOR DIABETES INSIPIDUS OF PITUITARY ORIGIN. IF POLYURIA IS DUE TO DEFICIENCY IN SECRETION OF NEUROHYPOPHYSIS, NORMAL URINE VOL CAN BE RESTORED BY ADMIN OF ANTIDIURETIC PRINCIPLE IN ANY FORM.
SUSTAINED ABSORPTION CAN BE ATTAINED BY NASAL INSUFFLATION OF APPROX 40 MG OF DRY POSTERIOR PITUITARY POWDER @ INTERVALS OF 6 TO 10 HR. EVEN MORE EFFECTIVE CONTROL OF URINE VOL IS ACHIEVED BY IM INJECTION OF VASOPRESSIN TANNATE IN OIL. DOSE MUST BE ADJUSTED TO INDIVIDUAL & RANGES AROUND 0.25 ML (1.25 UNITS) DAILY. /TANNATE/
ANTIDIURETIC PRINCIPLE IS USEFUL IN VARIETY OF DIAGNOSTIC TESTS. CONCENTRATING CAPACITY OF KIDNEY CAN BE RAPIDLY DETERMINED BY INJECTING 5-10 UNITS OF SUITABLE PREPN IM & MEASURING SPECIFIC GRAVITY OF URINE VOIDED 1 & 2 HR LATER.
/DIAGNOSTIC/ TEST HAS ADVANTAGE THAT IT MAY BE CARRIED OUT ON UNPREPARED PT, IS RAPIDLY EXECUTED, & IS MORE RELIABLE THAN WATER DEPRIVATION IN EDEMATOUS INDIVIDUALS. ...CAN BE ADMIN 15 TO 20 MIN PRIOR TO INJECTION OF CONTRAST MEDIA FOR IV UROGRAPHY, TO ENSURE MAX CONCN OF CONTRAST MATERIAL IN URINARY TRACT.
DESPITE ITS UNFORTUNATELY CHOSEN NAME, VASOPRESSIN SHOULD NOT BE EMPLOYED AS PRESSOR AGENT. IF IT IS DESIRED TO PRODUCE SYSTEMIC PERIPHERAL VASOCONSTRICTION, PREFERENCE SHOULD BE GIVEN TO APPROPRIATE SYMPATHOMIMETIC AMINES THAT CAN INCR PERIPHERAL RESISTANCE WITHOUT REDUCING CORONARY BLOOD FLOW.
...JUSTIFIABLE EXCEPTION MAY BE MADE FOR USE OF VASOPRESSIN AS ADJUNCT IN CONTROL OF BLEEDING ESOPHAGEAL VARICES & DURING ABDOMINAL SURGERY IN PT WITH PORTAL HYPERTENSION. ...HAS BEEN USED IN RELIEF OF INTESTINAL PARESIS & DISTENTION. DOSE OF 5-10 UNITS IS GIVEN BY IM INJECTION.
ACTION OF VASOPRESSIN HAS ALSO BEEN UTILIZED PRIOR TO CHOLECYSTOGRAPHY IN ORDER TO REMOVE GAS FROM BOWEL.
VASOPRESSIN TANNATE IN PEANUT OIL SUSPENSION IS MOST COMMONLY USED INJECTION PREPN FOR TREATMENT OF NEUROHYPOPHYSEAL DIABETES INSIPIDUS. TANNATE FORM PROVIDES MORE COMPLETE CONTROL OF MODERATE TO SEVERE POLYURIA THAN DO TOPICAL PREPN. ANTIDIURETIC EFFECT OF SINGLE DOSE LASTS 1-3 DAYS IN MOST PT. /TANNATE/
ADH IN AQ SOLN MAY BE GIVEN BY IV, IM, OR SC ROUTE & BY NASAL INSUFFLATION OF POWDERS OR SPRAYS. DUE TO RAPID INACTIVATION, EFFECTS ARE BRIEF AFTER IV ADMIN UNLESS HORMONE IS GIVEN BY CONTINUOUS INFUSION.
VET: EXPTL, IN STUDIES OF HEMODYNAMICS. ...IT HAS STIMULATING EFFECT ON SMOOTH MUSCLE OF INTESTINAL & URINARY TRACTS INCL BLADDER, ...ITS USE MAY HELP CONTROL POLYURIA OF DIABETES INSIPIDUS IN DOGS. TANNATE FORM IN PEANUT OIL IS USED IM OR SC FOR MORE PROLONGED ACTION THAN THAT PROVIDED BY AQ FORM.
INVESTIGATIONALLY, IN PROVOCATIVE TESTING FOR /PITUITARY RELEASE OF/ GROWTH HORMONE & CORTICOTROPIN...10 UNITS FOR ADULTS & 300 MICROUNITS/KG BODY WT FOR CHILDREN /IM/.
【Biomedical Effects and Toxicity】
UPON REACHING CIRCULATION...INJECTED ADH IS RAPIDLY REMOVED. ITS HALF-LIFE IN PLASMA, IN CONCN WITHIN PHYSIOLOGICAL RANGE, IS APPROX 15 MIN IN MAN. ADH IS REMOVED FROM PLASMA & INACTIVATED LARGELY DURING PASSAGE THROUGH LIVER & KIDNEYS. PORTION...IS ENZYMATICALLY INACTIVATED /BY KIDNEY/. REMAINDER APPEARS IN URINE...
URINARY CLEARANCE OF ADH IS 5-10% OF GLOMERULAR FILTRATION RATE. ...CIRCULATING ADH IS LARGELY UNBOUND &...CONFINED TO EXTRACELLULAR FLUID.

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