Doxycycline hydrochloride
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Doxycycline hydrochloride
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CAS No:
10592-13-9
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Formula:
C22H24N2O8.ClH
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Chemical Name:
Doxycycline hydrochloride
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Synonyms:
2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,hydrochloride (1:1),(4S,4aR,5S,5aR,6R,12aS)-;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride,[4S-(4α,4aα,5α,5aα,6α,12aα)]-;2-Naphthacenecarboxamide,4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,hydrochloride;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride,(4S,4aR,5S,5aR,6R,12aS)-;Deoxy-5-hydroxytetracycline hydrochloride;Doxycycline hydrochloride;Deoxyoxytetracycline hydrochloride;6-Deoxyoxytetracycline hydrochloride;α-6-Deoxy-5-hydroxytetracycline hydrochloride;Doxylin;Vibramycin hyclate;Vibramycin hydrochloride;Idocyklin;6-Desoxy-5-hydroxytetracycline hydrochloride;Farcodoxin;100929-47-3;53108-42-2;61281-03-6
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CAS No:
Description
Yellow Crystalline powderChEBI: The hydrochloride salt of doxycycline.Doxycycline hydrochloride is the hydrochloride form of doxycycline, being a tetracycline antibiotic that has enjoyed widespread use in both veterinary and human medicine owing to its relatively broad spectrum and wide margin of safety. The first members of the tetracycline class were isolated from several species of bacteria from the genus Streptomyces in the1940s and 1950s. Since that time, a variety of tetracycline have bee
Doxycycline Hydrochloride is the hydrochloride salt form of doxycycline exhibiting antimicrobial activity. Doxycycline blocks binding of aminoacyl-tRNA to the mRNA-ribosome complex, thereby inhibiting protein synthesis. In addition, this agent has exhibited inhibition of collagenase activity. (NCI)|A synthetic tetracycline derivative with similar antimicrobial activity.
Doxycycline hydrochloride Basic Attributes
480.9
480.129944
234-198-7
4182Z6T2ET
756751|633557
DTXSID4041020|DTXSID1045405
C29010
29413000
Characteristics
182
1.15470
yellow
1.63 g/cm3
195-201℃
762.6°C at 760 mmHg
87℃
soluble in water.H2O: 50 mg/mL, clear, yellow-green
0-6°C
195.6 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
NA 1993 / PGIII
3
22-36/37/38
26-36/37
Xn,Xi
Stable under normal shipping and handling conditions.
|Danger|H302 (80.26%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 152 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P263, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 15 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)
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-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-
Doxycycline hydrochloride Use and Manufacturing
Pd black (7.00 mg, 0.0657 mmol, 1.75 equiv) was added in one portion to a solution of the pentacyclic phenol MGC28 (25.0 mg, 0.0375 mmol, 1.0 equiv) in tetrahydrofuran-methanol (1:1, 2.0 mL) at 23 °C. An atmosphere of hydrogen was introduced by briefly evacuating the flask, then flushing with pure hydrogen (1 atm). The Pd catalyst was initially present as a fine dispersion, but aggregated into clumps within 5 min. The yellow heterogeneous mixture was stirred at 23 °C for 2 h, then was filtered through a plug of cotton. The filtrate was concentrated, affording a yellow oil (>95percent doxycycline based on 1H NMR analysis). The product was purified by preparatory HPLC on a Phenomenex Polymerx DVB column (10 μM, 250 x 10 mm, flow rate 4.0 mL/min, Solvent A: methanol-0.005 N aq. HCl (1:4), Solvent B: acetonitrile) using an injection volume of solvent A (400 μL) containing oxalic acid (10 mg) and an isochratic elution of 5percent B for 2 min, then a gradient elution of 5-50percent B for 20 min. The peak eluting at 12-17 min was collected and concentrated, affording (-)- doxycycline hydrochloride as a yellow powder (16.2 mg, 90percent), which was identical with natural (-)-doxycycline hydrochloride in all respects. [00187] 'H NMR (600 MHz, CD30D, hydrochloride) 5 7.47 (t, 1H, J= 8.4 Hz, ArH), 6.93 (d, 1 H, J = 8.4 Hz, ArH), 6.83 (d, 1 H, J = 8.4 Hz, ArH), 4.40 (s, 1H, (CH3)2NCH), 3.53 (dd, 1H, J= 12.0, 8.4 Hz, CHOH), 2.95 (s, 3H, N(CH3)CH3'), 2.88 (s, 3H, N(CH3)CH3'), 2.80 (d, 1H, J= 12.0 Hz, CHCHN (CH3)2), (dq, 1H, J= 12.6, 6.6 Hz, CH3CH), 2.58 (dd, lH, J= 12.6, 8.4 Hz, CH3CHCH), 1.55 (d, 3H, J= 6.6 Hz, CH3CHCH) ; 13C NMR (100 MHz, CD30D) No. 195.3, 188.2, 173.8, 172.1, 163.2, 149.0, 137.7, 117.1, 116.9, 116.6, 108.4, 96.0, 74.5, 69.8, 66.9, 47.5, 43.4, 43.0, 41.9, 40.0, 16.3; UV max (0.01 N methanolic HCl), nm 218, 267, 350; [α]D =-109° (c = 0.16 in 0.01 M methanolic HCl) ; lit. (The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 12th ed. Budavari, S. ; O'Neal, M. J. ; Smith, A.; Heckelman, P. E. ; Kinneary, J. F. , Eds. ; Merck Co. : Whitehouse Station, NJ, 1996; entry 3496. ) UV max (0.01 N methanolic HCI), nm 267, 351; [α]D=-110° (c = 1 in 0.01 M methanolic HCI); HRMS (ES) m/z calcd for (C22H24O8N2+H) + 445.1611, found 445.1603.
Doxycycline hydrochloride is a salt prepared from doxycycline taking advantage of the basic dimethylamino group which protonates and readily forms a salt in hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, doxycycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis.
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Computed Properties
Molecular Weight:480.9
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:2
Exact Mass:480.1299435
Monoisotopic Mass:480.1299435
Topological Polar Surface Area:182
Heavy Atom Count:33
Complexity:956
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Tetracycline antibiotics. This product is a broad-spectrum antibacterial agent with bactericidal effects at high concentrations. Rickettsia, Mycoplasma, Chlamydia, atypical mycobacteria, and spirochetes are also sensitive to this product. This product is more effective against Gram-positive bacteria than Gram-negative bacteria, but Enterococcus is resistant to it. Others such as Actinomycetes, Bacillus anthracis, Listeria monocytogenes, Clostridium, Nocardia, Vibrio, Brucella, Campylobacter, and Yersinia are sensitive to this product. This product has certain antibacterial activity against Neisseria gonorrhoeae, but penicillin-resistant Neisseria gonorrhoeae is also resistant to doxycycline. Due to the widespread use of tetracyclines over the years, common clinical pathogens have become seriously resistant to this product, including Gram-positive bacteria such as Staphylococcus and most Gram-negative bacilli.
Registered Holders
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Beijing Ansenbo Pharmaceutical Technology Co., Ltd.
Active
China
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Suzhou NO.5 Pharmaceutical FACTORY Co., Ltd.
Active
China
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Huashu Shanhe Pharmaceutical Co., Ltd.
Active
China
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