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Lanoconazole

READ AT http://newdrugapprovals.org/2014/10/02/lanoconazole/

Latoconazole, Lanoconazole, TJN-318, NND-318, Astat,

Nihon Nohyaku (Originator), Tsumura (Licensee)

Synonym:	2-[4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile
Application:	An antifungal compound
CAS Number:	101530-10-3
Molecular Weight:	319.83
Molecular Formula:	C₁₄H₁₀ClN₃S₂

Brief background information

Technical Information

Appearance:	Crystalline
Physical State:	Solid
Solubility:	Soluble in chloroform, and methanol. Insoluble in water.
Storage:	Store at -20° C
Melting Point:	129-132 °C
Boiling Point:	~477.6 °C at 760 mmHg (Predicted)
Density:	~1.4 g/cm³ (Predicted)
Refractive Index:	n²⁰_D 1.73 (Predicted)
pK Values:	pK_b: 3.76 (Predicted)

Safety and Reference Information

WGK Germany:	3
RTECS:	NI3393500
PubChem CID:	3002820
Merck Index:	14: 5357
MDL Number:	MFCD00865590
Beilstein Registry:	4819111

Salt	ATC	Formula	MM	CAS
–	D01	C ₁₄ H ₁₀ ClN ₃ S ₂	319.84 g / mol	101530-10-3

Lanoconazole

Application

antifungal

Synthesis pathway

Synthesis a)

Synthetic route

The reaction of 2- (1-imidazolyl) acetonitrile (I) with CS2 and KOH in DMF gives the dithiolate (II), which is then cyclized with 1- (2-chlorophenyl) -1,2-di (methanesulfonyloxy) ethane . (III) A column chromatography over silicagel allows the separation of the (E) -.? and (Z) -isomers (1-5)

Description Crystals, mp 141-5 Manufacturer Nihon Nohyaku Co., Ltd. (Japan) and Tsumura Juntendo (Japan).

References 1. Seo, A., Kanno, H., Hasegawa, N. et al. (Nihon Nohyaku Co., Ltd.). Antimycotic agent and fungicidal agent. US 4738976. 2. Seo, A ., Sugano, H., Hasegawa, C., Ikeda, K., Munechica, Y., Konoe, T., Konaka, M. (Nihon Nohyaku Co., Ltd.). Antifungal agent. JP 87093227. 3. Seo , A., Sugano, H., Hasegawa, C., Ikeda, K., Nishimura, A., Miyashiro, Y. (Nihon Nohyaku Co., Ltd.). Non-medicinal bactericidal agents and method for their preparation. JP 87093204. 4. Seo, A., Sugano, H., Hasegawa, C., Miyashiro, Y., Nishimura, A., Ikeda, K. (Nihon Nohyaku Co., Ltd.). Ketene S, S-acetals. JP 85218387. 5. Seo, A., Kanno, H., Hasegawa, N. et al. (Nihon Nohyaku Co., Ltd.). A novel ketene S, S-acetal deriv., a process for manufacturing thereof and a method for curing mycosis by administering it. EP 218736.

Trade Names

Country	Trade name	Manufacturer
Japan	Astatine	Tsumura
Ukraine	No	No

Formulations

1% cream;
1% ointment;
1% solution

Links

EP 218 736 (Nihon Nohyaku; EP-prior. 9.10.1985).

References

1. Oka, H., et al., 1992. Therapeutic efficacy of latoconazole in formulations of clinical use on experimental dermatophytosis in guinea pigs. Arzneimittel-Forschung. 42(3): 345-9. PMID: 1497697
2. Niwano, Y., et al., 1994. Therapeutic efficacy of lanoconazole, a new imidazole antimycotic agent, for experimental cutaneous candidiasis in guinea pigs. Antimicrobial agents and chemotherapy. 38(9): 2204-6. PMID: 7811048

3 http://aac.asm.org/content/38/9/2204.full.pdf

Title: Lanoconazole

CAS Registry Number: 101530-10-3

CAS Name: (E)-(±)-a-[4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene]-1H-imidazole-1-acetonitrile

Additional Names: latoconazole

Manufacturers’ Codes: TJN-318; NND-318

Trademarks: Astat (Nihon Nohyaku)

Molecular Formula: C14H10ClN3S2

Molecular Weight: 319.83

Percent Composition: C 52.57%, H 3.15%, Cl 11.08%, N 13.14%, S 20.05%

Literature References: Prepn: A. Soe et al., JP Kokai 85 218387; idem et al., US 4636519 (1985, 1987 both to Nihon Nohyaku).In vivo antifungal activity: H. Oka et al., Arzneim.-Forsch. 42, 345 (1992); Y. Niwano et al., Antimicrob. Agents Chemother. 38,2204 (1994). Toxicity study: P. L. Munt et al., Oyo Yakuri 43, 195 (1992).

Properties: Light yellow crystals, mp 141.5°. LD50 in male, female mice, rats (mg/kg): 3224, 2715, 993, 652 orally; 2158, 1743, 1655, 2596 i.p.; >5000 both species s.c. LD50 dermally in rats: >5000 mg/kg (Munt).

Melting point: mp 141.5°

Toxicity data: LD50 in male, female mice, rats (mg/kg): 3224, 2715, 993, 652 orally; 2158, 1743, 1655, 2596 i.p.; >5000 both species s.c.; LD50 dermally in rats: >5000 mg/kg (Munt)

Therap-Cat: Antifungal.

Keywords: Antifungal (Synthetic); Imidazoles.