Metacycline
Chemical compound
- J01AA05 (WHO)
- (2Z,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylene-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione
- 914-00-1 N
- 54675785
- 10468596 Y
- IR235I7C5P
- ChEMBL249837 N
- 001301
- DTXSID2023272
- Interactive image
- NC(=O)C=3C(=O)[C@@]4(O)C(\O)=C2\C(=O)c1c(O)cccc1C(=C)[C@H]2[C@H](O)[C@H]4[C@H](N(C)C)C=3O
InChI
- InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1 Y
- Key:MHIGBKBJSQVXNH-IWVLMIASSA-N Y
Metacycline or methacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.[citation needed]
It has been found to act as an agonist of the human pregnane X receptor ligand-binding domain and to induce CYP3A4 expression in vitro.[1]
References
- ^ Shukla SJ, Sakamuru S, Huang R, Moeller TA, Shinn P, Vanleer D, Auld DS, Austin CP, Xia M (2011). "Identification of clinically used drugs that activate pregnane X receptors" (PDF). Drug Metab. Dispos. 39 (1): 151–9. doi:10.1124/dmd.110.035105. PMC 3014269. PMID 20966043.
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- Agonists: 6,7-Dimethylesculetin
- Amiodarone
- Artemisinin
- Benfuracarb
- Carbamazepine
- Carvedilol
- Chlorpromazine
- Chrysin
- CITCO
- Clotrimazole
- Cyclophosphamide
- Cypermethrin
- DHEA (prasterone)
- Efavirenz
- Ellagic acid
- Griseofulvin
- Methoxychlor
- Mifepristone
- Nefazodone
- Nevirapine
- Nicardipine
- Octicizer
- Permethrin
- Phenobarbital
- Phenytoin
- Pregnanedione (5β-dihydroprogesterone)
- Reserpine
- TCPOBOP
- Telmisartan
- Tolnaftate
- Troglitazone
- Valproic acid
- Antagonists: 3,17β-Estradiol
- 3α-Androstanol
- 3α-Androstenol
- 3β-Androstanol
- 17-Androstanol
- AITC
- Ethinylestradiol
- Meclizine
- Nigramide J
- Okadaic acid
- PK-11195
- S-07662
- T-0901317
- Agonists: 17α-Hydroxypregnenolone
- 17α-Hydroxyprogesterone
- Δ4-Androstenedione
- Δ5-Androstenediol
- Δ5-Androstenedione
- AA-861
- Allopregnanediol
- Allopregnanedione (5α-dihydroprogesterone)
- Allopregnanolone (brexanolone)
- Alpha-Lipoic acid
- Ambrisentan
- AMI-193
- Amlodipine besylate
- Antimycotics
- Artemisinin
- Aurothioglucose
- Bile acids
- Bithionol
- Bosentan
- Bumecaine
- Cafestol
- Cephaloridine
- Cephradine
- Chlorpromazine
- Ciglitazone
- Clindamycin
- Clofenvinfos
- Chloroxine
- Clotrimazole
- Colforsin
- Corticosterone
- Cyclophosphamide
- Cyproterone acetate
- Demecolcine
- Dexamethasone
- DHEA (prasterone)
- DHEA-S (prasterone sulfate)
- Dibunate sodium
- Diclazuril
- Dicloxacillin
- Dimercaprol
- Dinaline
- Docetaxel
- Docusate calcium
- Dodecylbenzenesulfonic acid
- Dronabinol
- Droxidopa
- Eburnamonine
- Ecopipam
- Enzacamene
- Epothilone B
- Erythromycin
- Famprofazone
- Febantel
- Felodipine
- Fenbendazole
- Fentanyl
- Flucloxacillin
- Fluorometholone
- Griseofulvin
- Guggulsterone
- Haloprogin
- Hetacillin potassium
- Hyperforin
- Hypericum perforatum (St John's wort)
- Indinavir sulfate
- Lasalocid sodium
- Levothyroxine
- Linolenic acid: α-Linolenic acid and γ-linolenic acid
- LOE-908
- Loratadine
- Lovastatin
- Meclizine
- Metacycline
- Methylprednisolone
- Metyrapone
- Mevastatin
- Mifepristone
- Nafcillin
- Nicardipine
- Nicotine
- Nifedipine
- Nilvadipine
- Nisoldipine
- Norelgestromin
- Omeprazole
- Orlistat
- Oxatomide
- Paclitaxel
- Phenobarbital
- Piperine
- Plicamycin
- Prednisolone
- Pregnanediol
- Pregnanedione (5β-dihydroprogesterone)
- Pregnanolone
- Pregnenolone
- Pregnenolone 16α-carbonitrile
- Proadifen
- Progesterone
- Quingestrone
- Reserpine
- Reverse triiodothyronine
- Rifampicin
- Rifaximin
- Rimexolone
- Riodipine
- Ritonavir
- Simvastatin
- Sirolimus
- Spironolactone
- Spiroxatrine
- SR-12813
- Suberoylanilide
- Sulfisoxazole
- Suramin
- Tacrolimus
- Tenylidone
- Terconazole
- Testosterone isocaproate
- Tetracycline
- Thiamylal sodium
- Thiothixene
- Thonzonium bromide
- Tianeptine
- Troglitazone
- Troleandomycin
- Tropanyl 3,5-dimethulbenzoate
- Zafirlukast
- Zeranol
- Antagonists: Ketoconazole
- Sesamin
- See also
- Receptor/signaling modulators
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