Drug Information

General Information
Drug ID
DR00666
Drug Name
Doxycycline
Synonyms
(2E,4S,4aR,5S,5aR,6R,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (2Z)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (2Z,4S,4aR,5S,5aR,6R)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (2Z,4S,4aR,5S,5aR,6R,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aR,5S,5aR,6R,12aS); 5-Hydroxy-alpha-6-deoxytetracycline; 6-Deoxyoxytetracycline; 6-Deoxytetracycline; 6-alpha-Deoxy-5-oxytetracycline; 6alpha-Deoxy-5-oxytetracycline; Alpha-6-Deoxy-5-hydroxytetracycline; Alpha-6-Deoxyoxytetracycline; Alpha-Doxycycline; Alti-Doxycycline; Apo-Doxy; Atridox; Azudoxat; BMY-28689; BU-3839T; DMSC (*Fosfatex); DOXCYCLINE ANHYDROUS; DOXY; DOXYCYCLINE CALCIUM; DOXYCYCLINE MONOHYDRATE; Deoxymykoin; Dossiciclina; Dossiciclina [DCIT]; Doxiciclina; Doxiciclina [INN-Spanish]; Doxiciclina [Italian]; Doxitard; Doxivetin; Doxy-Caps; Doxy-Puren; Doxy-Tabs; Doxycen; Doxychel; Doxychel (TN); Doxycin; Doxycyclin; Doxycycline (200mg/day) or Placebo; Doxycycline (INN); Doxycycline (TN); Doxycycline (anhydrous); Doxycycline (internal use); Doxycycline anhydrous; Doxycycline hyclate; Doxycycline-Chinoin; Doxycyclinum; Doxycyclinum [INN-Latin]; Doxysol; Doxytec; Doxytetracycline; GS-3065 (*monohydrate); Hydramycin; Investin; Jenacyclin; Liviatin; Monodox; Monodox (*monohydrate); Novo-Doxylin; Nu-Doxycycline; Oracea; Periostat (TN); Ronaxan; Spanor; Supracyclin; Vibra-tabs; Vibramycin; Vibramycin (*monohydrate); Vibramycin Novum; Vibramycine; Vibravenos; Vivox (*Hyclate)
Drug Type
Small molecular drug
Indication Bacterial infections [ICD11:1A00-1H0Z] Approved [1]
Therapeutic Class
Antiinflammatory Agents
Structure
3D MOL 2D MOL
Formula
C22H24N2O8
Canonical SMILES
CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
InChI
InChI=1S/C22H24N2O8/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/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChIKey
SGKRLCUYIXIAHR-AKNGSSGZSA-N
CAS Number
CAS 564-25-0
Pharmaceutical Properties Molecular Weight 444.4 Topological Polar Surface Area 182
Heavy Atom Count 32 Rotatable Bond Count 2
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 9
XLogP
-0.7
PubChem CID
54671203
PubChem SID
11335520 ,11360759 ,11363701 ,11366263 ,11368825 ,11371256 ,11374272 ,11376987 ,11461731 ,11483982 ,11487959 ,11490224 ,11492342 ,11494621 ,14759559 ,14881664 ,22391429 ,26755247 ,29279579 ,39289952 ,39460532 ,46171207 ,46487965 ,46506491 ,47216696 ,47440169 ,47810665 ,47885321 ,47885322 ,47959651 ,49994878 ,50071302 ,50110882 ,53787282 ,56310727 ,56310911 ,56310919 ,56311074 ,56311250 ,56311566 ,56311567 ,56311897 ,56311928 ,56312054 ,56312284 ,56312312 ,56312315 ,596105 ,7979130 ,9187
ChEBI ID
ChEBI:50845
TTD Drug ID
D0S0LZ
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 Doxycycline was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.

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