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Mebendazole

Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations Reference
Mebendazole
Mebendazole structure
CAS No.
31431-39-7
Chemical Name:
Mebendazole
Synonyms
mbdz;Mebex;telmin;r17635;vermox;lomper;noverme;verpanyl;vermirax;bantenol
CBNumber:
CB8700094
Molecular Formula:
C16H13N3O3
Formula Weight:
295.29
MOL File:
31431-39-7.mol

Mebendazole Properties

Melting point:
288.5°C
Boiling point:
436.98°C (rough estimate)
Density 
1.1952 (rough estimate)
refractive index 
1.6500 (estimate)
storage temp. 
0-6°C
solubility 
Practically insoluble in water, in alcohol and in methylene chloride.
form 
neat
pka
pKa 3.43/9.93(H2O,t =25,I=0.025) (Uncertain)
Merck 
14,5768
BRN 
759809
CAS DataBase Reference
31431-39-7(CAS DataBase Reference)
EPA Substance Registry System
Carbamic acid, (5-benzoyl-1H-benzimidazol- 2-yl)-, methyl ester(31431-39-7)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xn
Risk Statements  22
Safety Statements  36
RIDADR  UN 2811
WGK Germany  3
RTECS  EY8600000
HS Code  29339900
Toxicity LD50 orally: >80 mg/kg in sheep; >40 mg/kg in mice, rats and chickens (Van Gelder)

Mebendazole price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich M2523 Mebendazole analytical standard, ≥98% (HPLC) 31431-39-7 25g $56.1 2018-11-20 Buy
Sigma-Aldrich 1375502 Mebendazole United States Pharmacopeia (USP) Reference Standard 31431-39-7 200mg $352.8 2018-11-20 Buy
TCI Chemical M2273 Mebendazole >98.0%(HPLC)(N) 31431-39-7 5g $25 2018-11-22 Buy
TCI Chemical M2273 Mebendazole >98.0%(HPLC)(N) 31431-39-7 25g $77 2018-11-22 Buy
Cayman Chemical 18872 Mebendazole ≥98% 31431-39-7 25g $47 2018-11-13 Buy

Mebendazole Chemical Properties,Uses,Production

Pharmacology and mechanism of action

Mebendazole is a benzimidazole derivative with a broad spectrum of anthelminthic activity. It is highly effective against adult and larval stages of Ascaris lumbricoides, Enterobius vermicularis, Trichuris trichiura, hookworms (Ancylostoma duodenale and Necator americanus) and Capillaria philippinensis. It is also ovicidal against Ascaris lumbricoides and Trichuris trichuria [1]. With high doses, the drug has some effect against hydatid disease [2]. Recent in vitro studies have reported mebendazole to be more effective than metronidazole in killing Giardia lamblia [3,4]; however, clinical findings are inconclusive [5, 6, 7]. The mechanisms of action of benzimidazoles are similar. These drugs appear to bind to parasite tubules with subsequent inhibition of the polymerization of tubules to microtubules which is vital for the normal functioning of the parasite cells[8].

Indications

Mebendazole is the drug of choice for mixed nematode infections due to Trichuris trichiura, Ascaris lumbricoides, Enterobius vermicularis, Capillaria philippinensis or hookworms. The drug may be used against hydatid disease when albendazole is not available.

Side effects

Despite the widespread use of the drug, few side effects have been reported, especially in patients with heavy infections. These include transitory abdominal pain, diarrhoea and slight headache. High doses of the drug such as those used in the treatment of hydatid disease have been associated with bone marrow toxicity, alopecia, hepatitis, glomerulonephritis, fever and exfoliative dermatitis [9–12].

Contraindications and precautions

When high doses of mebendazole are given, regular monitoring of serum-transaminase levels and leukocyte and platelet counts must be carried out. In patients with liver impairment dosage reductions must be made.

Interactions

The concomitant administration of phenytoin or carbamazepine has been reported to lower the plasma concentration of mebendazole [12], while cimetidine had the opposite effect[13].

Preparations

• Pantelmin® (Janssen). Oral solution 20 mg/ml. Tablets 100 mg, 500 mg. • Vermox® (Janssen). Oral suspension 20 mg/ml. Tablets 100 mg, 500 mg. Several other preparations are available.

Reference

1. Van den Bossche H, Rochette F, Horig C (1982). Mebendazole and related anthelminthics. Adv Pharmacol Chemother, 19, 287–296.
2. Todorov T, Vutova K, Mechkov G, Georgiev P, Petkov D, Tonchev Z, Nedelkov G (1992). Chemotherapy of human cystic echinococcosis: comparative efficacy of mebendazole and albendazole. Ann Trop Med Parasitol, 86, 59–66.
3. Cedillo-Rivera R, Munoz O (1992). In-vitro susceptibility of Giardia lamblia to albendazole, mebendazole and other chemotherapeutic agents. J Med Microbiol, 37, 221–224.
4. Edlind TD, Hang TL, Chakraborty PR (1990). Activity of the anthelminthic benzimidazoles against Giardia lamblia in vitro. J Infect Dis, 162, 1408–1411.
5. Al-Waili D, Al-Waili B, Saloom K (1988). Therapeutic use of mebendazole in giardial infections. Trans R Soc Trop Med Hyg, 82, 438.
6. Al-Waili NSD, Hasan NU (1992). Mebendazole in giardial infections: A comparative study with metronidazole. J Infect Dis, 165, 1170–1171.
7. Gascon J, Moreno A, Valls ME, Miro JM, Corachan M (1989). Failure of mebendazole treatment in Giardia lamblia infection. Trans R Soc Trop Med Hyg, 83, 647.
8. Lacey E (1990). Mode of action of Benzimidazoles. Parasitology Today, 6, 112–115.
9. Wilson JF, Rausch RL, McMahon BJ, Schantz PM (1992). Parasitological effect of chemotherapy in alveolar hydatid disease: Review of experience with mebendazole and albendazole in Alaskan eskimos. Clin. Infect Dis, 15, 234–249.
10. Ellis M, von Sinner W, Al-hokail A, Siek JA (1992). Clinical-radiological evaluation of benzimidazoles in the management of Echinococcus granulosus cysts. Scand J Infect Dis, 24, 1–13.
11. Todorov T, Vutova K, Mechkov G, Tonchev Z, Georgiev P, Lazarova I (1992). Experience in the chemotherapy of severe, inoperable echinococcosis in man. Infection, 20, 23–24.
12. Luder PJ, Siffert B, Witassek F, Meister F, Bircher J (1986). Treatment of hydatid disease with high oral doses of mebendazole. Long-term follow-up of plasma mebendazole levels and drug interactions. Eur J Clin Pharmacol, 31, 443–448.
13. Bekhti A, Pirotte J (1987). Cimetidine increases serum mebendazole concentrations. Implications for treatment of hepatic hydatid cysts. Br J Clin Pharmacol, 24, 390–392.

Chemical Properties

White Amorphous Powder

Uses

Anthelmintic (Nematodes)

Uses

For the treatment of Enterobius vermicularis (pinworm), Trichuris trichiura (whipworm), Ascaris lumbricoides (common roundworm), Ancylostoma duodenale (common hookworm), Necator americanus (American hookworm) in single or mixed infections.

Definition

ChEBI: A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.

Indications

Unlike thiabendazole, mebendazole (Vermox) does not inhibit fumarate reductase.While mebendazole binds to both mammalian and nematode tubulin, it exhibits a differential affinity for the latter, possibly explaining the selective action of the drug. The selective binding to nematode tubulin may inhibit glucose absorption, leading to glycogen consumption and ATP depletion.

brand name

Vermox (McNeil).

General Description

White to slightly yellow powder. Pleasant taste. Practically water insoluble.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Mebendazole is a carbamate ester-amine. Amines behave as chemical bases. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Fire Hazard

Flash point data for Mebendazole are not available; however, Mebendazole is probably combustible.

Pharmaceutical Applications

A benzimidazole carbamic acid methyl ester available for oral administration. It is insoluble in water and stable at room temperature.

Mechanism of action

Mebendazole is given orally; it is poorly soluble, and very little is absorbed from the intestinal tract. About 5 to 10%, principally the decarboxylated derivatives, is recovered in the urine; most of the orally administered drug is found in the feces within 24 hours.

Pharmacokinetics

Oral absorption is poor. Plasma concentrations achieved after oral administration of 100 mg every 12 h for three consecutive days do not exceed 0.03 mg/L. All metabolites are inactive. Most of the dose, as unchanged drug or a primary metabolite, is retained in the intestinal tract and passed in the feces, with the remainder, approximately 2% of the dose, excreted in the urine.

Clinical Use

Methyl 5-benzoyl-2-benzimidazolecarbamate (Vermox) isa broad-spectrum anthelmintic that is effective against variousnematode infestations, including whipworm, pinworm,roundworm, and hookworm. Mebendazole irreversiblyblocks glucose uptake in susceptible helminths, thereby depletingglycogen stored in the parasite. It apparently does notaffect glucose metabolism in the host. It also inhibits cell divisionin nematodes.
Mebendazole is poorly absorbed by the oral route.Adverse reactions are uncommon and usually consist of abdominaldiscomfort. It is teratogenic in laboratory animalsand, therefore, should not be given during pregnancy.

Clinical Use

Mebendazole is used primarily for the treatment of A. lumbricoides, T. trichiura, E. vermicularis, and hookworm infections, in which it produces high cure rates. It is an alternative agent for the treatment of trichinosis and visceral larva migrans. Owing to its broad-spectrum anthelmintic effect, mixed infections (ascariasis, hookworm infestation, or enterobiasis in association with trichuriasis) frequently respond to therapy. High doses have been used to treat hydatid disease, but albendazole is now thought to be superior.

Clinical Use

Intestinal nematode infections
Trichinosis (larval stage)

Side effects

Abdominal discomfort and diarrhea may occur when the worm load is heavy. Its use is contraindicated during pregnancy.

Side effects

Diarrhea and gastrointestinal discomfort may occur, but adverse reactions are generally mild. Woman of childbearing age should be informed of a potential risk to the fetus if treated during pregnancy, particularly during the first trimester.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Human mutation data reported. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

Mebendazole Preparation Products And Raw materials

Raw materials

Preparation Products


Mebendazole Suppliers

Global( 244)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2543 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1861 55
Hebei Minshang Biotechnology Co., Ltd
+86-13582176207
cathy@hbminshang.com CHINA 272 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30002 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23976 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 sales@jushengtech.com CHINA 28236 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930501651
breeduan@crovellbio.com CHINA 2314 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
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View Lastest Price from Mebendazole manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-05-20 Mebendazole
31431-39-7
US $10.00 / KG 1KG 99.9% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2018-07-23 Mebendazole
31431-39-7
US $96.00 / KG 1KG 99.5 100kg career henan chemical co

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