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9005-49-6

Basic Information
CAS No.: 9005-49-6
Name: Heparin
Article Data: 6
Molecular Structure:
Molecular Structure of 9005-49-6 (Heparin)
Formula: Unspecified
Molecular Weight: 1134.93
Synonyms: Ardeparin;AVE 5026;Centaxarin;CY 222;CY 216;Bemiparin;Arteven;Multiparin;Nadroparin;Nadroparine;Novoheparin;OP 386;OP 622;Octaparin;Pabyrn;Parnaparin;Reviparin;Subeparin;Tinzaparin;Vetren;a-Heparin;LipoHep Forte;KB 101;Heparin sulfate;Hapacarin;H 5284;Fraxiparin;Fragmin A;F 202;Clivarine;Clevarin;Mono-embolex;
EINECS: 232-681-7
Density: 2.13g/cm3
Melting Point: 250 °C (decomp)
Boiling Point: 644.9oC at 760mmHg
Flash Point: 343.8oC
Appearance: white crystalline powder
Safety: 24/25
PSA: 652.39000
LogP: -4.52610
Synthetic route
heparin sodium salt

heparin sodium salt

heparin

heparin

Conditions
ConditionsYield
With Amberlit IR-124 In water at 36.85℃; Equilibrium constant; Kinetics; Further Variations:; Reagents;
1333107-97-3

C22H34N2O

heparin

heparin

retinoic acid-heparin conjugate

retinoic acid-heparin conjugate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In formamide; N,N-dimethyl-formamide at 20℃; for 0.0833333h; microfluidics;95.3%
197151-85-2

2-aminoethylfolic acid γ-amide

1333107-97-3

C22H34N2O

heparin

heparin

folic acid-heparin-retinoic acid conjugate

folic acid-heparin-retinoic acid conjugate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In formamide; N,N-dimethyl-formamide at 20℃; for 0.0833333h; microfluidics;90.2%
2450-71-7

Propargylamine

heparin

heparin

propargylamine modified heparin

propargylamine modified heparin

Conditions
ConditionsYield
With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 48h; pH=6 - 6.5;78%
heparin

heparin

LMWH; N-deacetylated

LMWH; N-deacetylated

Conditions
ConditionsYield
With hydrazinium sulfate; hydrazine In water at 95℃; for 16h;16%
heparin

heparin

rat serum albumin

rat serum albumin

albumin-heparin conjugate

albumin-heparin conjugate

Conditions
ConditionsYield
With hydrogenchloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water at 4℃; for 24h; pH=5.0 - 7.6;
heparin sodium salt

heparin sodium salt

heparin

heparin

Conditions
ConditionsYield
With Amberlit IR-124 In water at 36.85℃; Equilibrium constant; Kinetics; Further Variations:; Reagents;
poly(vinyl amine)

poly(vinyl amine)

66-25-1

hexanal

heparin

heparin

poly(N-vinyl hexyl amine-co-N-vinyl heparin amine)

poly(N-vinyl hexyl amine-co-N-vinyl heparin amine)

Conditions
ConditionsYield
sodium cyanoborohydride In methanol; water for 48h;
heparin

heparin

O-desulfated heparin

O-desulfated heparin

Conditions
ConditionsYield
Stage #1: heparin With sodium tetrahydroborate In water at 25℃;
Stage #2: With sodium hydroxide pH=13; frozen and lyophilized to dryness;
hyaluronic acid (molecular weight 150.000 Dalton)

hyaluronic acid (molecular weight 150.000 Dalton)

heparin

heparin

heparin-Hy complex

heparin-Hy complex

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfate In water pH=1.48;
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  • Heparin CAS NO.9005-49-6

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History

 Heparin (CAS NO.9005-49-6) is discovered in 1916 predates the establishment of the Food and Drug Administration of the United States, although it did not enter clinical trials until 1935.It was originally isolated from canine liver cells, hence its name. Heparin's discovery can be attributed to the research activities of two men, Jay McLean and William Henry Howell.

Specification

1. Introduction of Heparin
Heparin is one kind of wihte or alomost white powder. The IUPAC name of Heparin is (4S,6R)-6-[(2R,4R)-4,6-Dihydroxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-3,4-dihydroxy-5-sulfonatooxyoxane-2-carboxylate. The Classification Code of this chemical is Anticoagulants ; Cardiovascular Agents ; Drug / Therapeutic Agent ; Fibrin Modulating Agents ; Fibrinolytic agents ; Hematologic Agents ; Human Data ; Mutation data ; Natural Product ; Reproductive Effect. Heparin can soluble in water.

2. Properties of Heparin
Physical properties about Heparin are:
(1)XLogP3-AA: -10.8; (2)H-Bond Donor: 15; (3)H-Bond Acceptor: 38; (4)Rotatable Bond Count: 21; (5)Tautomer Count: 2; (6)Exact Mass: 1134.006995; (7)MonoIsotopic Mass: 1134.006995; (8)Topological Polar Surface Area: 652; (9)Heavy Atom Count: 70; (10)Formal Charge: 0; (11)Complexity: 2410; (12)Isotope Atom Count: 0; (13)Defined Atom Stereocenter Count: 0; (14)Undefined Atom Stereocenter Count: 20; (15)Defined Bond Stereocenter Count: 0; (16)Undefined Bond Stereocenter Count: 0; (17)Covalently-Bonded Unit Count: 1; (18)Index of Refraction: 1.711; (19)Molar Refractivity: 190.48 cm3; (20)Molar Volume: 486.7 cm3; (21)Surface Tension: 148.8 dyne/cm; (22)Density: 2.13 g/cm3.

3. Structure Descriptors of Heparin
(1)InChI: InChI=1S/C26H42N2O37S5/c1-4(30)27-7-9(31)13(6(56-23(7)39)3-55-67(43,44)45)58-26-19(65-70(52,53)54)12(34)16(20(62-26)22(37)38)60-24-8(28-66(40,41)42)15(63-68(46,47)48)14(5(2-29)57-24)59-25-18(64-69(49,50)51)11(33)10(32)17(61-25)21(35)36/h5-20,23-26,28-29,31-34,39H,2-3H2,1H3,(H,27,30)(H,35,36)(H,37,38)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,
49,50,51)(H,52,53,54)
(2)InChIKey: HTTJABKRGRZYRN-UHFFFAOYSA-N
(3)Canonical SMILES : CC(=O)NC1C(C(C(OC1O)COS(=O)(=O)O)OC2C(C(C(C(O2)C(=O)O)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)C(=O)O)O)O)OS(=O)(=O)O)OS(=O)(=O)O)NS(=O)(=O)O)O)OS(=O)(=O)O)O

4. Toxicity of Heparin

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 3536units/kg/ (3536units/kg)   Southern Medical Journal. Vol. 80, Pg. 1450, 1987.
man TDLo subcutaneous 1857units/kg/ (1857units/kg)   Southern Medical Journal. Vol. 80, Pg. 1450, 1987.
man TDLo subcutaneous 1857units/kg/ (1857units/kg) CARDIAC: OTHER CHANGES Southern Medical Journal. Vol. 80, Pg. 1450, 1987.
mouse LD50 intraperitoneal 1900mg/kg (1900mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 60, Pg. 507, 1964.
mouse LD50 intravenous 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1366, 1986.
mouse LD50 subcutaneous 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS
Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1366, 1986.
rat LD50 oral 1950mg/kg (1950mg/kg)   German Offenlegungsschrift Patent Document. Vol. #2636091,
rat LDLo intraperitoneal 420mg/kg (420mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
women TDLo subcutaneous 30uL/kg/5D-I (.03mL/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Journal of Haematology. Vol. 82, Pg. 620, 1992.
women TDLo subcutaneous 48mg/kg/20D-I (48mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BLOOD: HEMORRHAGE
Australian and New Zealand Journal of Medicine. Vol. 28, Pg. 59, 1998.
women TDLo subcutaneous 1000units/kg/ (1000units/kg)   Southern Medical Journal. Vol. 80, Pg. 1450, 1987.

5. Safety information of Heparin
S24/25: Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: MI0850000
F: 3-10
Moderately toxic by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

6. Uses of Heparin
Heparin (CAS NO.9005-49-6) may sometimes be used to treat sports injuries. Heparin, also known as unfractionated heparin, a highly sulfated glycosaminoglycan, is widely used as an injectable anticoagulant, and has the highest negative charge density of any known biological molecule. It can also be used to form an inner anticoagulant surface on various experimental and medical devices such as test tubes and renal dialysis machines.