Metacycline

Metacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.

Metacycline
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01AA05 (WHO)
Identifiers
IUPAC name (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
CAS Number	914-00-1^N
PubChem CID	54675785
ChemSpider	10468596^Y
UNII	IR235I7C5P
ChEMBL	ChEMBL249837^N
NIAID ChemDB	001301
CompTox Dashboard (EPA)	DTXSID2023272
ECHA InfoCard	100.011.834
Chemical and physical data
Formula	C₂₂H₂₂N₂O₈
Molar mass	442.419 g/mol g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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
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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.

Xenobiotic-sensing receptor modulators
CAR	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
PXR	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 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 Nuclear receptor modulators

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