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ID
DB00251|APRD00659||
名称
Terconazole
描述
Terconazole is an anti-fungal drug that is mainly used to treat vaginal yeast infections (or vaginal candidiasis). It is classified as a _triazole ketal derivative_.[A178096] Terconazole was initially approved by the FDA in 1987.[FDA label] This drug is available in cream and suppository forms and both have demonstrated high levels of safety, efficacy, and tolerability in clinical trials. [A178093]
cas号
67915-31-5
唯一标识码
0KJ2VE664U
状态
solid
一般参考文献
Thomason JL: Clinical evaluation of terconazole. United states experience. J Reprod Med. 1989 Aug;34(8 Suppl):597-601.
Pfaller MA, Gerarden T: Susceptibility of clinical isolates of Candida spp. to terconazole and other azole antifungal agents. Diagn Microbiol Infect Dis. 1989 Nov-Dec;12(6):467-71.


组
approved,
指示
For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.
药效学
Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.
作用机制
Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.
毒性
The oral LD50 values were found to be 1741 and 849 mg/kg for the male and female in rat.
代谢
Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.
吸收
Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations
半衰期
6.9 hours (range 4.0-11.3)
分类
description:This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
direct-parent:Phenylpiperazines
kingdom:Organic compounds
superclass:Organoheterocyclic compounds
class:Diazinanes
subclass:Piperazines
alternative-parent:1,3-dioxolanes
alternative-parent:Alkyl aryl ethers
alternative-parent:Aminophenyl ethers
alternative-parent:Aniline and substituted anilines
alternative-parent:Aryl chlorides
alternative-parent:Azacyclic compounds
alternative-parent:Dialkylarylamines
alternative-parent:Dichlorobenzenes
alternative-parent:Heteroaromatic compounds
alternative-parent:Hydrocarbon derivatives
alternative-parent:Ketals
alternative-parent:N-alkylpiperazines
alternative-parent:N-arylpiperazines
alternative-parent:Organochlorides
alternative-parent:Organopnictogen compounds
alternative-parent:Oxacyclic compounds
alternative-parent:Phenoxy compounds
alternative-parent:Trialkylamines
alternative-parent:Triazoles
substituent:1,2,4-triazole
substituent:1,3-dichlorobenzene
substituent:Acetal
substituent:Alkyl aryl ether
substituent:Amine
substituent:Aminophenyl ether
substituent:Aniline or substituted anilines
substituent:Aromatic heteromonocyclic compound
substituent:Aryl chloride
substituent:Aryl halide
substituent:Azacycle
substituent:Azole
substituent:Benzenoid
substituent:Chlorobenzene
substituent:Dialkylarylamine
substituent:Ether
substituent:Halobenzene
substituent:Heteroaromatic compound
substituent:Hydrocarbon derivative
substituent:Ketal
substituent:Meta-dioxolane
substituent:Monocyclic benzene moiety
substituent:N-alkylpiperazine
substituent:N-arylpiperazine
substituent:Organic nitrogen compound
substituent:Organic oxygen compound
substituent:Organochloride
substituent:Organohalogen compound
substituent:Organonitrogen compound
substituent:Organooxygen compound
substituent:Organopnictogen compound
substituent:Oxacycle
substituent:Phenol ether
substituent:Phenoxy compound
substituent:Phenylpiperazine
substituent:Tertiary aliphatic amine
substituent:Tertiary aliphatic/aromatic amine
substituent:Tertiary amine
消除途径
Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.
种类
Anti-Infective Agents
D000890
Antifungal Agents
D000935
Antifungal Agents (Vaginal)

Azole Antifungals

Genito Urinary System and Sex Hormones

Gynecological Antiinfectives and Antiseptics

Triazole Derivatives

盐类
蛋白质结合
94.9%
清除
同义词
language:english; code:inn/usan; name;Terconazole
国际品牌
Terazol
配送量
产品
name:Taro-terconazole Cream
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name:Terconazole Vaginal Cream 0.8%
labeller:E. Fougera & Co. a division of Fougera Pharmaceuticals Inc.
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ndc-product-code:0168-0347
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name:Zazole
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labeller:PharmaDerm a division of Fougera Pharmaceuticals Inc.
ndc-id:
ndc-product-code:0462-0346
dpd-id:
ema-product-code:
ema-ma-number:
started-marketing-on:2005-02-18
ended-marketing-on:2012-07-31
dosage-form:Cream
strength:4 mg/1g
route:Vaginal
fda-application-number:ANDA076712
generic:true
over-the-counter:false
approved:true
country:US
source:FDA NDC
混合物
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terazol 7
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terazol 7
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terazol 7
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terazol 3
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Zazole
ingredients:Terconazole
name:Zazole
ingredients:Terconazole
name:Zazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole Vaginal Cream 0.8%
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Terconazole
ingredients:Terconazole
name:Taro-terconazole Cream
ingredients:Terconazole
name:Terazol 3 Vaginal Ovules 80mg
ingredients:Terconazole
name:Terazol 3 Vaginal Cream 0.8%
ingredients:Terconazole
name:Terazol 3 Dual Pak
ingredients:Terconazole + Terconazole
name:Terazol 3 Dual Pak
ingredients:Terconazole + Terconazole
name:Terazol 7 Vaginal Cream 0.4%
ingredients:Terconazole
包装者
name:A-S Medication Solutions LLC
url:http://orders.a-smeds.com
name:Dept Health Central Pharmacy
url:
name:Dispensing Solutions
url:http://www.drxdispensing.com
name:Diversified Healthcare Services Inc.
url:http://www.dhscorp.com
name:E. Fougera and Co.
url:http://www.fougera.com
name:Lake Erie Medical and Surgical Supply
url:
name:Nycomed Inc.
url:http://www.nycomed.com
name:Ortho Mcneil Janssen Pharmaceutical Inc.
url:http://www.ortho-mcneil.com
name:Ortho-McNeil-Janssen Pharmaceuticals Inc.
url:http://www.ortho-mcneil.com
name:Perrigo Co.
url:http://www.perrigo.com
name:Pharmaderm
url:http://www.pharmaderm.com
name:Pharmedix
url:http://www.pharmedixrx.com
name:Physicians Total Care Inc.
url:http://www.physicianstotalcare.com
name:Rebel Distributors Corp.
url:http://www.rebelrx.com
name:Stat Rx Usa
url:http://statrxusa.exporterus.com
name:Taro Pharmaceuticals USA
url:http://www.tarousa.com
name:Watson Pharmaceuticals
url:http://www.watson.com
生产者
generic:否; url:; name;Ortho mcneil janssen pharmaceuticals inc
generic:是; url:; name;Altana inc
generic:是; url:; name;Nycomed us inc
generic:是; url:; name;Taro pharmaceuticals usa inc
generic:否; url:; name;Ortho mcneil janssen pharmaceutical inc
generic:是; url:; name;Perrigo new york inc
价格
Terazol 7 cream
1.17(单位：USD）
g
Terconazole 0.8% cream
2.35(单位：USD）
g
Zazole 0.8% vaginal cream
2.54(单位：USD）
g
Terazol 3 cream
2.64(单位：USD）
g
Terconazole 0.4% Cream 45 gm Tube
42.57(单位：USD）
tube
Terconazole 0.8% Cream 20 gm Tube
42.57(单位：USD）
tube
Terconazole 3 80 mg Suppository Box
50.9(单位：USD）
box
Terazol 3 3 80 mg Suppository Box
53.99(单位：USD）
box
Terazol 7 0.4% Cream 45 gm Tube
54.0(单位：USD）
tube
Terazol 3 0.8% Cream 20 gm Tube
55.99(单位：USD）
tube
Terconazole 0.4% cream
0.96(单位：USD）
g
受影响的生物体
Fungi
剂量
form:Cream
route:Vaginal
strength:0.8 g
form:Insert
route:Vaginal
strength:80 mg
form:Insert
route:Vaginal
strength:200 mg
form:Insert
route:Vaginal
strength:100 mg
form:Cream
route:Vaginal
strength:
form:Suppository
route:Vaginal
strength:80 mg/1
form:Cream; insert; kit
route:Vaginal
strength:
form:Insert
route:Vaginal
strength:
form:
route:Vaginal
strength:240 MG
form:
route:Vaginal
strength:40 MG
form:
route:Vaginal
strength:80 MG
form:Cream
route:Vaginal
strength:0.4 %
form:Cream
route:Vaginal
strength:0.8 %
form:Cream
route:Vaginal
strength:4 mg/1g
form:Cream
route:Vaginal
strength:8 mg/1g
form:Cream
route:Vaginal
strength:3.58 mg
atc代码
Triazole derivatives
ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
GENITO URINARY SYSTEM AND SEX HORMONES
fda标签
//s3-us-west-2.amazonaws.com/drugbank/fda_labels/DB00251.pdf?1557344183
化学品安全技术说明书
专利
食物相互作用
药物相互作用
序列
实验性质
Melting Point
126.3 °C

logP
4.5

外部标识符
resource：Drugs Product Database (DPD)
identifier：1197
resource：ChEBI
identifier：82980
resource：PubChem Compound
identifier：441383
resource：PubChem Substance
identifier：46505257
resource：KEGG Compound
identifier：C08080
resource：KEGG Drug
identifier：D00888
resource：ChemSpider
identifier：390122
resource：BindingDB
identifier：50375318
resource：PharmGKB
identifier：PA164768834
resource：Therapeutic Targets Database
identifier：DAP000629
resource：Wikipedia
identifier：Terconazole
resource：ChEMBL
identifier：CHEMBL1306
resource：ZINC
identifier：ZINC000003873936
resource：RxCUI
identifier：37806
外部链接
RxList
http://www.rxlist.com/cgi/generic/tercon.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ter1436.shtml
Drugs.com
http://www.drugs.com/cdi/terconazole-cream.html
路径
目标
id:BE0000233
name:Cytochrome P450 51
organism:Yeast
action:antagonist
Vanden Bossche H, Marichal P: Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1193-9.
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
Cauwenbergh G, Vanden Bossche H: Terconazole. Pharmacology of a new antimycotic agent. J Reprod Med. 1989 Aug;34(8 Suppl):588-92.
known-action:yes
name:Lanosterol 14-alpha demethylase
general-function:Sterol 14-demethylase activity
specific-function:Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
gene-name:ERG11
locus:
cellular-location:Membrane
transmembrane-regions:
signal-regions:
theoretical-pi:7.19
molecular-weight:60674.965
chromosome-location:
organism:Yeast
external-identifiers:GenBank Gene DatabaseX13296GenBank Protein Database578119UniProtKBP10613UniProt AccessionCP51_CANAL
synonyms:1.14.13.70CYP51CYPLICytochrome P450 51Cytochrome P450-14DMCytochrome P450-LIA1ERG16Sterol 14-alpha demethylase
amino-acid-sequence:>lcl|BSEQ0010022|Lanosterol 14-alpha demethylase MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPLVFYWIPWFGS AASYGQQPYEFFESCRQKYGDVFSFMLLGKIMTVYLGPKGHEFVFNAKLSDVSAEDAYKH LTTPVFGKGVIYDCPNSRLMEQKKFAKFALTTDSFKRYVPKIREEILNYFVTDESFKLKE KTHGVANVMKTQPEITIFTASRSLFGDEMRRIFDRSFAQLYSDLDKGFTPINFVFPNLPL PHYWRRDAAQKKISATYMKEIKSRRERGDIDPNRDLIDSLLIHSTYKDGVKMTDQEIANL LIGILMGGQHTSASTSAWFLLHLGEKPHLQDVIYQEVVELLKEKGGDLNDLTYEDLQKLP SVNNTIKETLRMHMPLHSIFRKVTNPLRIPETNYIVPKGHYVLVSPGYAHTSERYFDNPE DFDPTRWDTAAAKANSVSFNSSDEVDYGFGKVSKGVSSPYLPFGGGRHRCIGEQFAYVQL GTILTTFVYNLRWTIDGYKVPDPDYSSMVVLPTEPAEIIWEKRETCMF
gene-sequence:>lcl|BSEQ0010023|Lanosterol 14-alpha demethylase (ERG11) ATGGCTATTGTTGAAACTGTCATTGATGGCATTAATTATTTTTTGTCCCTTAGTGTTACA CAACAGATCAGTATATTATTAGGGGTTCCATTTGTTTACAACTTAGTATGGCAATATTTA TATTCATTAAGAAAAGATAGAGCTCCATTAGTGTTTTATTGGATTCCTTGGTTTGGTTCT GCAGCTTCATATGGTCAACAACCTTATGAATTTTTCGAATCATGTCGTCAAAAGTATGGT GATGTATTTTCATTTATGTTATTAGGGAAAATTATGACGGTTTATTTAGGTCCAAAAGGT CATGAATTTGTTTTTAATGCTAAATTATCTGATGTTTCTGCTGAAGATGCTTATAAACAT TTAACTACTCCAGTTTTCGGTAAAGGGGTTATTTATGATTGTCCAAATTCCAGATTAATG GAACAAAAAAAATTTGCTAAATTTGCTTTGACTACTGATTCATTTAAAAGATATGTTCCT AAGATTAGAGAAGAAATTTTGAATTATTTTGTTACTGATGAAAGTTTCAAATTGAAAGAA AAAACTCATGGGGTTGCCAATGTTATGAAAACTCAACCAGAAATTACTATTTTCACTGCT TCAAGATCTTTATTTGGTGATGAAATGAGAAGAATTTTTGACCGTTCATTTGCTCAACTA TATTCTGATTTAGATAAAGGTTTTACCCCTATTAATTTTGTTTTCCCTAATTTACCTTTA CCTCATTATTGGAGACGTGATGCTGCTCAAAAGAAAATCTCTGCTACTTATATGAAAGAA ATTAAACTGAGAAGAGAACGTGGTGATATTGATCCAAATCGTGATTTAATTGATTCCTTA TTGATTCATTCAACTTATAAAGATGGTGTGAAAATGACTGATCAAGAAATTGCTAATCTT TTAATTGGTATTCTTATGGGTGGTCAACATACTTCTGCTTCTACTTCTGCTTGGTTCTTG TTACATTTAGGTGAAAAACCTCATTTACAAGATGTTATTTATCAAGAAGTTGTTGAATTG TTGAAAGAAAAAGGTGGTGATTTGAATGATTTGACTTATGAAGATTTACAAAAATTACCA TCAGTCAATAACACTATTAAGGAAACTCTTAGAATGCATATGCCATTACATTCTATTTTT AGAAAAGTTACTAACCCATTAAGAATCCCTGAAACCAATTATATTGTTCCAAAAGGTCAT TATGTTTTAGTTTCTCCAGGTTATGCTCATACTAGTGAAAGATATTTTGATAACCCTGAA GATTTTGATCCAACTAGATGGGATACTGCTGCTGCCAAAGCTAATTCTGTTTCATTTAAC TCTTCTGATGAAGTTGATTATGGGTTTGGGAAAGTTTCTAAAGGGGTTTCTTCACCTTAT TTACCATTTGGTGGTGGTAGACATAGATGTATTGGGGAACAATTTGCTTATGTTCAATTG GGAACCATTTTAACTACTTTTGTTTATAACTTAAGATGGACTATTGATGGTTATAAAGTG CCTGACCCTGATTATAGTTCAATGGTGGTTTTACCTACTGAACCAGCAGAAATCATTTGG GAAAAAAGAGAAACTTGTATGTTTTAA
pfams:PF00067p450
go-classifiers:componentendoplasmic reticulumcomponentintegral component of membranecomponentmembranecomponentplasma membranefunctiondrug bindingfunctionheme bindingfunctioniron ion bindingfunctionsterol 14-demethylase activityprocesscell growth mode switching, budding to filamentousprocesscellular response to drugprocessdemethylationprocessergosterol biosynthetic processprocessmembrane raft polarizationprocessoxidation-reduction process
酶
载体
运输工具
药物反应
效应
不良反应

目录