Tetracycline phosphateProduct ingredient for Tetracycline

Name
Tetracycline phosphate
Drug Entry
Tetracycline

Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells.

The FDA withdrew its approval for the use of all liquid oral drug products formulated for pediatric use containing tetracycline in a concentration greater than 25 mg/ml.2 Other formulations of tetracycline continue to be used.

Accession Number
DBSALT001631
Structure
Synonyms
Not Available
UNII
NZ662XY5PP
CAS Number
13930-32-0
Weight
Average: 542.434
Monoisotopic: 542.130161315
Chemical Formula
C22H27N2O12P
InChI Key
WXDJNRXQVCECPF-IZGCTLQUSA-N
InChI
InChI=1S/C22H24N2O8.H3O4P/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;1-5(2,3)4/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);(H3,1,2,3,4)/t9-,10-,15-,21-,22-;/m0./s1
IUPAC Name
(4S,4aS,5aS,6R,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; phosphoric acid
SMILES
OP(O)(O)=O.[H][C@@]12C[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C)C(=O)C1=C(C=CC=C1O)[C@]3(C)O
ChemSpider
32700551
Predicted Properties
PropertyValueSource
Water Solubility1.33 mg/mLALOGPS
logP-0.56ALOGPS
logP-3.5Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.26Chemaxon
pKa (Strongest Basic)9.25Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area181.62 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity114.19 m3·mol-1Chemaxon
Polarizability42.04 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon