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76963-41-2

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Basic Information
CAS No.: 76963-41-2
Name: Nizatidine
Molecular Structure:
Molecular Structure of 76963-41-2 (Nizatidine)
Formula: C12H21N5O2S2
Molecular Weight: 331.463
Synonyms: Niatidine;Nizatidine (JAN/USP);1,1-Ethenediamine; N-[2-[(dimethylamino) Mythyl]-4- Thiazolyl] Methyl] Ethyl]-Nmethyl-,2-nitro;Naxidine;Tazac;1,1-Ethenediamine, N-(2-(((2-((dimethylamino)methyl)-4-thiazolyl)methyl)thio)ethyl)-N-methyl-2-nitro-;Cronizat;Panaxid;1,1-Ethenediamine,N-[2-[[[2-[(dimethylamino)- methyl]-4-thiazolyl]methyl]thio]ethyl]-N'- methyl-2-nitro-;Nizatidina [Spanish];Antizid;Ulcosol;ZE-101;LY 139037;Axid (TN);Zanizal;1,1-Ethenediamine, N-(2-(((2-((dimethylamino)methyl)-4-thiazoly)methyl)thio)ethyl)-N-methyl-2-nitro-;Calmaxid;Ulxid;Splendil ER;Nizatidinum [Latin];Galitidin;N-(4-(6-Methylamino-7-nitro-2-thia-5-aza-6-hepten-1-yl)-2-thiazolylmethyl)-N,N-dimethylamin;Nizatidine [USAN:BAN:INN:JAN];Distaxid;
EINECS: 627-310-4
Density: 1.249 g/cm3
Melting Point: 130-132 °C
Boiling Point: 478.162 °C at 760 mmHg
Flash Point: 242.984 °C
Solubility: 21.4g/L(temperature not stated)
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
PSA: 139.55000
LogP: 2.62750
Synthetic route
102721-76-6, 61832-41-5

2-methylamino-2-methylthio-1-nitroethene

78441-62-0

4-[[(2-aminoethyl)thio]-methyl]-N,N-dimethyl-2-thiazolemethanamine

76963-41-2

nizatidine

Conditions
ConditionsYield
In water at 20 - 35℃; for 8h;81%
In water at 30℃; Temperature;80.6%
92759-37-0

4-Hydroxy-4-(chloromethyl)-2-<(dimethylamino)methyl>thiazoline

76963-41-2

nizatidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; potassium hydroxide / 4 h / 15 - 20 °C
2: hydrogen bromide / Reflux
3: water / 30 °C
View Scheme
76963-41-2

nizatidine

cucurbit[7]uril

C42H42N28O14*C12H21N5O2S2

Conditions
ConditionsYield
In water
Raw Materials
78441-62-0
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History

Nizatidine was developed by Eli Lilly, and was first marketed in 1987. It is considered to be equipotent with ranitidine and differs by the substitution of a thiazole-ring in place of the furan-ring in ranitidine.
In September 2000 Eli Lilly announced that they will sell the sales and marketing rights for Axid, to Reliant Pharmaceuticals. Subsequently, Reliant developed the oral solution of Axid and got approval by the U.S. Food and Drug Administration (FDA) in May 2004 and started marketing it.  However, a year later they sold rights of the Axid Oral Solution to Braintree Laboratories.

Specification

The Nizatidine, with the CAS registry number 76963-41-2, is also known as N-(4-(6-Methylamino-7-nitro-2-thia-5-aza-6-hepten-1-yl)-2-thiazolylmethyl)-N,N-dimethylamin. It belongs to the product categories of Active Pharmaceutical Ingredients; APIs; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Heterocycles; Sulfur & Selenium Compounds. This chemical's molecular formula is C12H21N5O2S2 and molecular weight is 331.46. What's more, its systematic name is N-{2-[({2-[(Dimethylamino)methyl]-1,3-thiazol-4-yl}methyl)sulfanyl]ethyl}-N'-methyl-2-nitro-1,1-ethenediamine. Its classification codes are: (1)Anti-ulcer agents; (2)Anti-ulcerative; (3)Drug / Therapeutic Agent. It is a histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers. It has also been used experimentally to control weight gain associated with some antipsychotic medication. This chemical is harmful if swallowed. When using it, you need to wear suitable protective clothing.

Physical properties of Nizatidine are:
(1)ACD/LogP: -0.486; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.15; (4)ACD/LogD (pH 7.4): -0.69; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 8.18; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 139.55 Å2; (13)Index of Refraction: 1.592; (14)Molar Refractivity: 89.823 cm3; (15)Molar Volume: 265.354 cm3; (16)Polarizability: 35.608×10-24cm3; (17)Surface Tension: 51.51 dyne/cm; (18)Density: 1.249 g/cm3; (19)Flash Point: 242.984 °C; (20)Enthalpy of Vaporization: 74.221 kJ/mol; (21)Boiling Point: 478.162 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)C=C(NC)NCCSCc1nc(sc1)CN(C)C
(2)Std. InChI: InChI=1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3
(3)Std. InChIKey: SGXXNSQHWDMGGP-UHFFFAOYSA-N

The toxicity data of Nizatidine is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intramuscular > 225mg/kg (225mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: TETANY

BEHAVIORAL: TREMOR
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
dog LD50 intravenous > 75mg/kg (75mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: TREMOR
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
dog LD50 oral > 800mg/kg (800mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
monkey LD50 intravenous > 200mg/kg (200mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
monkey LD50 oral > 1200mg/kg (1200mg/kg)   Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
mouse LD50 intravenous 232mg/kg (232mg/kg)   Drugs in Japan Vol. -, Pg. 920, 1995.
mouse LD50 oral 1630mg/kg (1630mg/kg)   Drugs in Japan Vol. -, Pg. 920, 1995.
mouse LD50 subcutaneous 1082mg/kg (1082mg/kg) BEHAVIORAL: COMA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
rat LD50 intravenous 301mg/kg (301mg/kg) BEHAVIORAL: COMA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.
rat LD50 oral 1653mg/kg (1653mg/kg)   Drugs in Japan Vol. -, Pg. 920, 1995.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: COMA
Fundamental and Applied Toxicology. Vol. 13, Pg. 778, 1989.