Nizatidine (Tazac, Axid, LY-139037, LY 139037, LY139037) is a potent histamine H2 receptor antagonist used in the treatment of peptic ulcer disease and gastroesophageal reflux disease. Its IC50 value for the histamine H2 receptor is 0.9 nM.

Physicochemical Properties

Molecular Formula	C12H21N5O2S2
Molecular Weight	331.46
Exact Mass	331.113
Elemental Analysis	C, 43.48; H, 6.39; N, 21.13; O, 9.65; S, 19.35
CAS #	76963-41-2
Related CAS #	Nizatidine-d3; 1246833-99-7
PubChem CID	3033637
Appearance	Off-white to light yellow-brown solid powder
Density	1.2±0.1 g/cm3
Boiling Point	478.2±45.0 °C at 760 mmHg
Melting Point	130-132ºC
Flash Point	243.0±28.7 °C
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.592
LogP	1.18
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Heavy Atom Count	21
Complexity	349
Defined Atom Stereocenter Count	0
SMILES	S(C([H])([H])C1=C([H])SC(C([H])([H])N(C([H])([H])[H])C([H])([H])[H])=N1)C([H])([H])C([H])([H])N([H])/C(=C(\[H])/[N+](=O)[O-])/N([H])C([H])([H])[H]
InChi Key	SGXXNSQHWDMGGP-IZZDOVSWSA-N
InChi Code	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/b11-6+
Chemical Name	(E)-1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
Synonyms	LY 139037; Tazac; Axid; LY-139037; LY139037
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Histamine H2 receptor ( IC50 = 0.9 nM ); AChE ( IC50 = 6.7 μM )
ln Vitro	In vitro activity: Nizatidine, a selective histamine H2-receptor antagonist, has an IC50 of 0.9 nM and is a strong inhibitor of gastric acid secretion.[1] Nizatidine additionally and noncompetitively inhibits acetylcholinesterase (AChE) with a Ki value of 7.4 μM and an IC50 of 6.7 μM. [2]
ln Vivo	Nizatidine shows a maximum suppression of stomach acid in rats during the first hour of medication administration (EC50 = 1.383 μmol/kg).[1] Nizatidine (0.3-3 mg/kg, i.v.) dramatically raises the motor index of gastrointestinal (GI) motility in a dose-dependent manner. Nizatidine has an ED50 and ED90 of 0.18 and 3.22 mg/kg in dogs and 2.94 and 19.6 mg/kg in rats, respectively, which means that it inhibits the secretion of stomach acid.[2]
Enzyme Assay	Nizatidine, a selective histamine H2-receptor antagonist, is a highly effective inhibitor of gastric acid secretion, with IC50 of 0.9 nM. Nizatidine has an EC50 of 1.383 μmol/kg and shows maximal inhibition of gastric acid in rats during the first hour of medication administration. Acetylcholinesterase (AChE) is likewise reversibly inhibited by nizatidine, with an IC50 of 6.7 μM and a noncompetitive inhibition with a Ki value of 7.4 μM. In a dose-dependent manner, nizatidine (0.3–3 mg/kg, intravenously) dramatically raises the motor index of gastrointestinal (GI) motility. With ED50 and ED90 values of 0.18 and 3.22 mg/kg in dogs and 2.94 and 19.6 mg/kg in rats, respectively, nizatidine suppresses the secretion of gastric acid.
Animal Protocol	Dissolved in saline; 0.5-10 μmol/kg; s.c. injection Rat
Toxicity/Toxicokinetics	Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Because of the low levels of nizatidine in breastmilk, amounts ingested by the infant are small and would not be expected to cause any adverse effects in breastfed infants. No special precautions are required. Histamine H2-antagonists with more extensive use might be preferred in newborns. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Histamine H2-receptor blockade is known to stimulate prolactin secretion. No reports of hyperprolactinemia, galactorrhea or effects on breastfeeding women caused by nizatidine were found as of the revision date. The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed.
References	[1]. J Pharmacol Exp Ther . 1986 Nov;239(2):406-10. [2]. J Pharmacol Exp Ther . 1993 Jan;264(1):152-7.
Additional Infomation	Nizatidine is a member of the class of 1,3-thiazoles having a dimethylaminomethyl substituent at position 2 and an alkylthiomethyl moiety at position 4. It has a role as an anti-ulcer drug, a H2-receptor antagonist and a cholinergic drug. It is a member of 1,3-thiazoles, a C-nitro compound, an organic sulfide, a tertiary amino compound and a carboxamidine. Nizatidine is a competitive and reversible histamine H2-receptor antagonist with antacid activity. Nizatidine inhibits the histamine H2-receptors located on the basolateral membrane of the gastric parietal cell, thereby reducing basal and nocturnal gastric acid secretion, resulting in a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli. A histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers. See also: Nizatidine (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO: ~66 mg/mL (~199.1 mM) Water: ~28 mg/mL (~84.5 mM) Ethanol: ~18 mg/mL (~54.3 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 3.5 mg/mL (10.56 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3.5 mg/mL (10.56 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 3.5 mg/mL (10.56 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 35.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: Saline: 30 mg/mL Solubility in Formulation 5: 50 mg/mL (150.85 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.0170 mL	15.0848 mL	30.1696 mL
	5 mM	0.6034 mL	3.0170 mL	6.0339 mL
	10 mM	0.3017 mL	1.5085 mL	3.0170 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.