Synonym
Anhydrotetracycline hydrochloride, Anhydrotetracycline HCl
IUPAC/Chemical Name
(4S,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Hydrochloride
InChi Key
XBSQEFHDCDFNJU-WPJNXPDPSA-N
InChi Code
InChI=1S/C22H22N2O7.ClH/c1-8-9-5-4-6-12(25)13(9)17(26)14-10(8)7-11-16(24(2)3)18(27)15(21(23)30)20(29)22(11,31)19(14)28;/h4-6,11,16,25-27,31H,7H2,1-3H3,(H2,23,30);1H/t11-,16-,22-;/m0./s1
SMILES Code
O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])CC3=C(C([C@@]21O)=O)C(O)=C4C(O)=CC=CC4=C3C)N.[H]Cl
Appearance
Yellow solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
462.88
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Sabharwal S, Kishore K, Moorthy PN. Determination of tetracycline hydrochloride in presence of anhydrotetracycline by differential pulse polarography. J Pharm Sci. 1988 Jan;77(1):78-80. doi: 10.1002/jps.2600770115. PMID: 3346827.
2: Pernarowski M, Searl RO, Naylor J. Application of absorbance ratios to analysis of pharmaceuticals. V. Analysis of tetracycline hydrochloride in presence of anhydrotetracycline and epianhydrotetracycline. J Pharm Sci. 1969 Apr;58(4):470-2. doi: 10.1002/jps.2600580418. PMID: 5787447.
3: Zha JP, Lin Y, Yang XH, Hou HN, Wei TJ, Chen XL. [Cetyltrimethylammonium bromide for fluorescence enhancement of anhydrotetracycline hydrochloride and iso-tetracycline]. Guang Pu Xue Yu Guang Pu Fen Xi. 2002 Jun;22(3):430-2. Chinese. PMID: 12938325.
4: Xie L, Wang C, Chen M, Jin BB, Zhou R, Huang Y, Hameed S, Ying Y. Temperature-dependent terahertz vibrational spectra of tetracycline and its degradation products. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Nov 5;222:117179. doi: 10.1016/j.saa.2019.117179. Epub 2019 May 28. PMID: 31202030.
5: Xu D, Xiao Y, Pan H, Mei Y. Toxic effects of tetracycline and its degradation products on freshwater green algae. Ecotoxicol Environ Saf. 2019 Jun 15;174:43-47. doi: 10.1016/j.ecoenv.2019.02.063. Epub 2019 Feb 25. PMID: 30818259.
6: Hussien EM. Development and validation of an HPLC method for tetracycline- related USP monographs. Biomed Chromatogr. 2014 Sep;28(9):1278-83. doi: 10.1002/bmc.3161. Epub 2014 Mar 12. PMID: 24619929.
7: Moreno-Cerezo JM, Córdoba-Díaz M, Córdoba-Díaz D, Córdoba-Borrego M. A stability study of tetracycline and tetracycline cyclodextrins in tablets using a new HPLC method. J Pharm Biomed Anal. 2001 Oct;26(3):417-26. doi: 10.1016/s0731-7085(01)00416-2. PMID: 11489387.
8: Dihuidi K, Roets E, Hoogmartens J, Vanderhaeghe H. Etude de la stabilité en solution méthanolique du chlorhydrate de tétracycline, chlorhydrate d'épi-4 tétracycline, chlorhydrate d'anhydrotéteracycline, chlorhydrate d'épi-4 anhydrotétracycline et chlorhydrate de chlortétracycline [Study of the stability in methanolic solution of tetracycline hydrochloride and some analogues (author's transl)]. J Pharm Belg. 1982 Jan-Feb;37(1):35-46. French. PMID: 7077511.
9: Dijkhuis IC. Rapid determination of anhydrotetracyclines in tetracycline hydrochloride. Pharm Weekbl. 1967 Dec 8;102(49):1308-13. PMID: 5584148.
10: Fike WW, Brake NW. Modified method for determining tetracycline, 4-epitetracycline, and anhydrotetracyclines in tetracycline base or hydrochloride. J Pharm Sci. 1972 Apr;61(4):615-7. doi: 10.1002/jps.2600610427. PMID: 5014324.
11: Klimova NE, Ermolova OB. Embriotoksichnost' i immunodepressivnoe deĭstvie tetratsiklina i ego épi- i angidroproizvodnykh [Embryotoxicity and the immunodepressive action of tetracycline and its epi- and anhydro- derivatives]. Antibiotiki. 1976 Nov;21(11):1018-22. Russian. PMID: 1035488.
12: Röper H, Heyns K. Zur Frage der Bildung von Dimethylnitrosamin aus Tetracyclin-Derivaten bei der Nitrosierung in saurer Lösung [On the problem of dimethylnitrosamine formation from tetracycline-derivatives by nitrosation reaction in acidic medium (author's transl)]. Z Naturforsch C Biosci. 1977 Sep- Oct;32(9-10):696-702. German. PMID: 22167.
