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Ethambutol hydrochloride

Ethambutol hydrochloride structure

CAS No:
1070-11-7
Formula:
C10H24N2O2.2ClH
Chemical Name:
Ethambutol hydrochloride
Synonyms:
1-Butanol,2,2′-(1,2-ethanediyldiimino)bis-,hydrochloride (1:2),(2S,2′S)-;1-Butanol,2,2′-(ethylenediimino)di-,dihydrochloride,(+)-;1-Butanol,2,2′-(1,2-ethanediyldiimino)bis-,dihydrochloride,[S-(R*,R*)]-;1-Butanol,2,2′-(1,2-ethanediyldiimino)bis-,dihydrochloride,(2S,2′S)-;CL 40881;Ethambutol dihydrochloride;Ethambutol hydrochloride;d-2,2′-(Ethylenediimino)-di-1-butanol dihydrochloride;Myambutol;(+)-2,2′-(Ethylenediimino)di-1-butanol dihydrochloride;Dadibutol;Sural;Mycobutol;Dexambutol;Ebutol;Tibutol;Ethambutold dihydrochloride;Etapiam;Etibi;Tambutol;25612-54-8;51575-55-4
Categories:
Organic Chemistry > Amides

Description

Ethambutol Dihydrochloride is a bacteriostatic antimycobacterial agent, which obstructs the formation of cell wall by inhibiting arabinosyl transferases.Target: AntibacterialEthambutol directly affects two polymers, arabinogalactan (AG) and lipoarabinomannan (LAM) in Mycobacterium smegmatis. In M. smegmatis, Ethambutol inhibits synthesis of arabinan completely and inhibits AG synthesis most likely as a consequence of this; more than 50% of the cell arabinan is released from the bacteria

Ethambutol Hydrochloride is the hydrochloride salt form of ethambutol, an ethylenediamine derivative with antibacterial activity, specifically effective against mycobacteria. Although the exact mechanism of action of ethambutol hydrochloride is unknown, ethambutol hydrochloride inhibits the transfer of mycolic acids into the cell wall of bacteria, which impedes bacterial cell growth. This agent may also interfere with RNA synthesis or inhibit other cell metabolism, thereby preventing cell multiplication and causing cell death.|An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863)

Ethambutol hydrochloride Basic Attributes

Molecular Weight：

277.23

Exact Mass：

276.137146

EC Number：

213-970-7

UNII：

QE4VW5FO07

DSSTox ID：

DTXSID4045345

NCI Thesaurus Code：

C29033

HScode：

2922191000

Characteristics

PSA：

64.5

XLogP3：

2.09320

Appearance：

white

Melting Point：

198.5-200.3 °C

Boiling Point：

345.3ºC at 760 mmHg

Flash Point：

113.7ºC

Water Solubility：

Slightly soluble in water

Storage Conditions：

Refrigerator

Vapor Pressure：

3.35E-07mmHg at 25°C

Specific rotation：

D25 +7.6° (c = 2 in water)

Collision Cross Section：

147 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

61-36/37/38

safety instructions：

53-22-36/37/39-45-36/37-26

RTECS Number：

EL3854000

Marks：

T,Xi

Precautionary statement(s)：

P201-P308 + P313

Hazard Statements：

H360

GHS Classification：

|Danger|H360 (97.67%): May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)

MeSH Entry Terms：

Dexambutol

Ethambutol hydrochloride Use and Manufacturing

Uses

Antibacterial (tuberculostatic)

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:277.23
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:276.1371335
Monoisotopic Mass:276.1371335
Topological Polar Surface Area:64.5
Heavy Atom Count:16
Complexity:109
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Synthetic antibacterial anti-tuberculosis drug. It has strong activity against bacteria in the growth and reproduction stage, and has almost no effect on bacteria in the dormant stage. It has high antibacterial activity against various types of mycobacteria. There is no cross-resistance between Mycobacterium tuberculosis and other drugs. It may inhibit the metabolism of sensitive bacteria, inhibit RNA synthesis, and interfere with the protein metabolism of Mycobacterium tuberculosis, thereby causing bacterial death. In large doses, it can cause cleft palate, brain exposure, and spinal deformity in mouse experiments; it can cause mild cervical deformity in rat experiments; it can cause cyclops, short limbs, and cleft palate in rabbit experiments.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Ethambutol hydrochloride
Manufacturer	Minsheng Group Shaoxing Pharmaceutical Co., Ltd.

Ethambutol Hydrochloride Capsules
Ingredients	Ethambutol hydrochloride, its chemical name is [2R, 2[S-(R, R)]-R]-()2,2-(1,2-ethylenediimino)-bis-1-butanol dihydrochloride
Indication	1 Aluminum salts, including DDI buffer, can reduce the absorption of this product. 2 The combination of this product with verapamil can reduce the absorption of the latter. 3 The combination with neurotoxic drugs can increase the neurotoxicity of this product, such as optic neuritis or peripheral neuritis. 4 The combination with ethionamide can increase the adverse reactions such as icteric hepatitis and optic neuritis.
Specifications	0.25 g
Manufacturer	Shenyang Kangzhi Pharmaceutical Co., Ltd.

Ethylamine, pyrazine, and rifampicin tablets (Ⅱ)
Ingredients	Each tablet contains 0.15g of rifampicin (C43H58N4O12), 0.075g of isoniazid (C6H7N3O), 0.4g of pyrazinamide (C5H5N3O), and 0.275g of ethambutol hydrochloride (C10H24N2O2·2HCl).
Indication	1. The effect of other drugs on this product: Antacids can reduce the bioavailability of rifampicin, isoniazid, and ethambutol. To avoid this situation, this product should be taken within 1 hour of taking anti-acids. Corticosteroids can reduce the blood concentration of isoniazid by promoting the metabolism of isoniazid and/or increasing renal clearance. 2. The effect of this product on other drugs: Rifampicin has a strong induction effect on the cytochrome P450 system (CYP450). The cytochrome P450 system is mainly composed of two subfamilies, CYP3A and CYP2C, which account for 80% of the cytochrome P450 system isoenzymes. When used in combination, rifampicin can accelerate the metabolism of the combined drugs. These drugs taken at the same time are partially or completely metabolized by these two isoenzymes. Rifampicin can also induce uridine-
Specifications	450 mg (C43H58N4O1275 mg, C6H7N3O37.5 mg, C5H5N3O200 mg and C10H24N2O2·2HCl137.5 mg)
Manufacturer	Zhejiang Sukean Pharmaceutical Co., Ltd.

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Registered Holders

LUPIN LIMITED

Brazil
Active
Biobetta Pharmaceuticals (Shanghai) Co., Ltd.

China
Active
Minsheng Group Shaoxing Pharmaceutical Co., Ltd.

China
Active

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