Doxycycline (hydrochloride)

CAT: 0804-HY-N0565A-01Size: 25 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-N0565A-01Size:25 mg

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Description

Doxycycline hydrochloride, an antibiotic, is an orally active and broad-spectrum metalloproteinase (MMP) inhibitor[1]. Doxycycline hydrochloride shows antibacterial activity and anti-cancer cell proliferation activity. Doxycycline hydrochloride can be used to construct gene expression regulation models[1][2][3][4][5].

CAS Number

10592-13-9

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Antibiotic; Bacterial; MMP; Parasite

Type

Reference compound

Related Pathways

Anti-infection; Metabolic Enzyme/Protease

Applications

COVID-19-immunoregulation

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/doxycycline-hydrochloride.html

Purity

99.99

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])[C@@H](O)[C@]3([H])[C@@H](C)C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4)N.Cl

Molecular Formula

C22H25ClN2O8

Molecular Weight

480.90

Precautions

H302, H315, H319, H335

References & Citations

[1]Wilfried Briest, et al. Doxycycline ameliorates the susceptibility to aortic lesions in a mouse model for the vascular type of Ehlers-Danlos syndrome. J Pharmacol Exp Ther. 2011 Jun;337 (3) :621-7.|[2]Eusebio Manchado, et al. A combinatorial strategy for treating KRAS-mutant lung cancer. Nature. 2016 Jun 30;534 (7609) :647-51.|[3]Anna-Luisa Luger, et al. Doxycycline Impairs Mitochondrial Function and Protects Human Glioma Cells from Hypoxia-Induced Cell Death: Implications of Using Tet-Inducible Systems. Int J Mol Sci. 2018 May 17;19 (5) :1504.|[4]Ethan Ahler, et al. Doxycycline alters metabolism and proliferation of human cell lines. PLoS One. 2013 May 31;8 (5) :e64561.|[5]Le Zhang, et al. Doxycycline inhibits the cancer stem cell phenotype and epithelial-to-mesenchymal transition in breast cancer. Cell Cycle. 2017 Apr 18;16 (8) :737-745.|[6]Niv Y. Doxycycline in Eradication Therapy of Helicobacter pylori--a Systematic Review and Meta-Analysis. Digestion. 2016;93 (2) :167-73.|[7]Manfredsson FP, et al. Tight Long-term dynamic doxycycline responsive nigrostriatal GDNF using a single rAAV vector. Mol Ther. 2009 Nov;17 (11) :1857-67.|[8]Kistner A, et al. Doxycycline-mediated quantitative and tissue-specific control of gene expression in transgenic mice. Proc Natl Acad Sci U S A. 1996 Oct 1;93 (20) :10933-8.

Shipping Conditions

Room Temperature

Storage Conditions

4°C (Powder, sealed storage, away from moisture)

Scientific Category

Reference compound1

Clinical Information

Launched

Isoform

Tetracycline

Citation 01

Chemical Information

Doxycycline Hydrochloride

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)

CAS Number	10592-13-9
PubChem CID	54685920
IUPAC Name	(4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;hydrochloride
Molecular Formula	C22H25ClN2O8
Molecular Weight	480.9
Topological Polar Surface Area	182
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Heavy Atom Count	33
Formal Charge	0
Complexity	956

SMILES

C[C@@H]1[C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O.Cl

InChI

InChI=1S/C22H24N2O8.ClH/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);1H/t7-,10+,14+,15-,17-,22-;/m0./s1

InChIKey

PTNZGHXUZDHMIQ-CVHRZJFOSA-N

Chemical Structure

2D Structure

CAS: 10592-13-9

CID: 54685920

Formula: C22H25ClN2O8

MW: 480.9

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
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 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	956
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

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