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Tetracyclines

Organic compounds comprising a linearly fused tetracyclic backbone to which a variety of functional groups can be attached; they have an octahydrotetracene-2-carboxamide skeleton, and are known as derivatives of polycyclic naphthacene carboxamide.
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1

Chlortetracycline hydrochloride

CAS: 64-72-2 Molecular Formula: C22H24Cl2N2O8 Molecular Weight (g/mol): 515.34 MDL Number: MFCD00082440 InChI Key: QYAPHLRPFNSDNH-CIVPRPTRSA-N Synonym: chlortetracycline hydrochloride,4-epi-chlortetracycline hydrochloride,2-amino hydroxy methylidene-7-chloro-4-dimethylamino-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride,2-azanyl oxidanyl methylidene-7-chloranyl-4-dimethylamino-6-methyl-6,10,11,12a-tetrakis oxidanyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride PubChem CID: 66577600 IUPAC Name: (4S,4aR,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride SMILES: CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl

PubChem CID 66577600
CAS 64-72-2
Molecular Weight (g/mol) 515.34
MDL Number MFCD00082440
SMILES CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl
Synonym chlortetracycline hydrochloride,4-epi-chlortetracycline hydrochloride,2-amino hydroxy methylidene-7-chloro-4-dimethylamino-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride,2-azanyl oxidanyl methylidene-7-chloranyl-4-dimethylamino-6-methyl-6,10,11,12a-tetrakis oxidanyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride
IUPAC Name (4S,4aR,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride
InChI Key QYAPHLRPFNSDNH-CIVPRPTRSA-N
Molecular Formula C22H24Cl2N2O8
2

Thermo Scientific Chemicals 4-Epioxytetracycline, 'can be used as secondary standard'

CAS: 14206-58-7 Molecular Formula: C22H24N2O9 Molecular Weight (g/mol): 460.43 MDL Number: MFCD00062825 InChI Key: OWFJMIVZYSDULZ-DVJPNYBFSA-N Synonym: 4-epioxytetracyline,unii-73von8sry5,4-epioxytetracycline,73von8sry5,4r,4ar,5s,5ar,6s,12as-4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide,hydroxy quatrimycin,oxytetracycline dihydrate specified impurity a ep,oxytetracycline hydrochloride specified impurity a ep,4r,4ar,5s,5ar,6s,12as-4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-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-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, 4r,4ar,5s,5ar,6s,12as PubChem CID: 54678403 IUPAC Name: (4R,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide SMILES: CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O

PubChem CID 54678403
CAS 14206-58-7
Molecular Weight (g/mol) 460.43
MDL Number MFCD00062825
SMILES CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O
Synonym 4-epioxytetracyline,unii-73von8sry5,4-epioxytetracycline,73von8sry5,4r,4ar,5s,5ar,6s,12as-4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide,hydroxy quatrimycin,oxytetracycline dihydrate specified impurity a ep,oxytetracycline hydrochloride specified impurity a ep,4r,4ar,5s,5ar,6s,12as-4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-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-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, 4r,4ar,5s,5ar,6s,12as
IUPAC Name (4R,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
InChI Key OWFJMIVZYSDULZ-DVJPNYBFSA-N
Molecular Formula C22H24N2O9
3

Chlortetracycline hydrochloride, specified according to the requirements of Ph.Eur.

CAS: 64-72-2 Molecular Formula: C22H23ClN2O8·HCl Molecular Weight (g/mol): 515.33 MDL Number: MFCD00082440 InChI Key: QYAPHLRPFNSDNH-CIVPRPTRSA-N Synonym: chlortetracycline hydrochloride,4-epi-chlortetracycline hydrochloride,2-amino hydroxy methylidene-7-chloro-4-dimethylamino-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride,2-azanyl oxidanyl methylidene-7-chloranyl-4-dimethylamino-6-methyl-6,10,11,12a-tetrakis oxidanyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride PubChem CID: 66577600 IUPAC Name: (4S,4aR,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride SMILES: CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl

PubChem CID 66577600
CAS 64-72-2
Molecular Weight (g/mol) 515.33
MDL Number MFCD00082440
SMILES CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl
Synonym chlortetracycline hydrochloride,4-epi-chlortetracycline hydrochloride,2-amino hydroxy methylidene-7-chloro-4-dimethylamino-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride,2-azanyl oxidanyl methylidene-7-chloranyl-4-dimethylamino-6-methyl-6,10,11,12a-tetrakis oxidanyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione hydrochloride
IUPAC Name (4S,4aR,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride
InChI Key QYAPHLRPFNSDNH-CIVPRPTRSA-N
Molecular Formula C22H23ClN2O8·HCl
4

Thermo Scientific Chemicals Metacycline hydrochloride, 98%, sec. Standard

CAS: 3963-95-9 Molecular Formula: C22H22N2O8·HCl Molecular Weight (g/mol): 478.9 MDL Number: MFCD04972012 InChI Key: VXPSARQTYDZXAO-CCHMMTNSSA-N Synonym: methacycline hydrochloride,methacycline hcl,adriamicina,ciclobiotic,germiciclin,rondomycin,metadomus,metacycline hydrochloride,globociclina,metilenbiotic PubChem CID: 54685047 IUPAC Name: (4S,4aR,5S,5aR,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride SMILES: CN(C)C1C2C(C3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O.Cl

PubChem CID 54685047
CAS 3963-95-9
Molecular Weight (g/mol) 478.9
MDL Number MFCD04972012
SMILES CN(C)C1C2C(C3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O.Cl
Synonym methacycline hydrochloride,methacycline hcl,adriamicina,ciclobiotic,germiciclin,rondomycin,metadomus,metacycline hydrochloride,globociclina,metilenbiotic
IUPAC Name (4S,4aR,5S,5aR,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride
InChI Key VXPSARQTYDZXAO-CCHMMTNSSA-N
Molecular Formula C22H22N2O8·HCl
5

Demeclocycline hydrochloride

CAS: 64-73-3 Molecular Formula: C21H22Cl2N2O8 Molecular Weight (g/mol): 501.313 MDL Number: MFCD00082371 InChI Key: OAPVUSSHCBRCOL-KBHRXELFSA-N Synonym: demeclocycline hydrochloride,demeclocycline hcl,declomycin,detravis,ledermycine,clortetrin,ledermycin,ledermicina,veraciclina,demeplus PubChem CID: 54686764 IUPAC Name: (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;hydrochloride SMILES: CN(C)C1C2CC3C(C4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O.Cl

PubChem CID 54686764
CAS 64-73-3
Molecular Weight (g/mol) 501.313
MDL Number MFCD00082371
SMILES CN(C)C1C2CC3C(C4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O.Cl
Synonym demeclocycline hydrochloride,demeclocycline hcl,declomycin,detravis,ledermycine,clortetrin,ledermycin,ledermicina,veraciclina,demeplus
IUPAC Name (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide;hydrochloride
InChI Key OAPVUSSHCBRCOL-KBHRXELFSA-N
Molecular Formula C21H22Cl2N2O8
6

Medchemexpress LLC Sancycline (Bonomycin; 6-demethyl-6-deoxytetracycline) | 808-26-4 | 98.0% | 414.41 | 100 MG
SDP

Sancycline (6-Demethyl-6-deoxytetracycline) acts by reversibly binding to the 30 S ribosomal subunit and inhibiting protein translation by blocking entry of aminoacyl-tRNA into the ribosome, similar to tetracycline. It is a semi-synthetic tetracycline prepared by hydrogenolysis of the chloro and benzylic hydroxy moieties of Declomycin. Sancycline has been shown to decrease 2 chloroethyl ethyl sulfide (CEES) and nitrogen mustard (NM) induced corneal injuries and inhibit Matrix metalloproteinase (MMP)-9 expression in the basement membrane zone (BMZ).

  • Reversibly binds to 30 S ribosomal subunit
  • Inhibits protein translation
  • Decreases CEES and NM induced corneal injuries
  • Inhibits MMP-9 expression

ENCOMPASS_PREFERRED
7

Medchemexpress LLC Oxytetracycline dihydrate | 6153-64-6 | 99.37% | 50 MG
SDP

Oxytetracycline dihydrate is an antibiotic of the tetracycline class. It is a potent inhibitor of both Gram-negative and Gram-positive bacteria. This compound acts as a protein synthesis inhibitor by preventing the binding of aminoacyl-tRNA to the m-ribosomal RNA complex. Additionally, it exhibits anti-HSV-1 activity.

  • Antibiotic belonging to the tetracycline class.
  • Potently inhibits Gram-negative and Gram-positive bacteria.
  • Acts as a protein synthesis inhibitor.
  • Possesses anti-HSV-1 activity.
  • Available in various quantities, including solid and solution forms.
  • High purity of 99.37%.

ENCOMPASS_PREFERRED
8

Medchemexpress LLC Oxytetracycline (dihydrate) | 6153-64-6 | 99.4% | 5 G
SDP

Oxytetracycline dihydrate is an antibiotic from the tetracycline class, known for its potent inhibition of Gram-negative and Gram-positive bacteria. It functions as a protein synthesis inhibitor by preventing the binding of aminoacyl-tRNA to the m-ribosomal RNA complex, and also demonstrates anti-HSV-1 activity.

  • Antibiotic belonging to the tetracycline class
  • Potently inhibits Gram-negative and Gram-positive bacteria
  • Acts as a protein synthesis inhibitor
  • Prevents binding of aminoacyl-tRNA to m-ribosomal RNA complex
  • Exhibits anti-HSV-1 activity

ENCOMPASS_PREFERRED
9

Medchemexpress LLC Oxytetracycline (dihydrate) | 6153-64-6 | 99.4% | 10 G
SDP

Oxytetracycline dihydrate is an antibiotic belonging to the tetracycline class. It potently inhibits both Gram-negative and Gram-positive bacteria by acting as a protein synthesis inhibitor, preventing the binding of aminoacyl-tRNA to the m-ribosomal RNA complex. This compound also exhibits anti-HSV-1 activity.

  • Potently inhibits Gram-negative and Gram-positive bacteria
  • Acts as a protein synthesis inhibitor
  • Exhibits anti-HSV-1 activity
  • Belongs to the tetracycline class of antibiotics
  • Classified as a phenol

ENCOMPASS_PREFERRED
10

Medchemexpress LLC Oxytetracycline dihydrate | 6153-64-6 | 99.4% | 500 MG
SDP

Oxytetracycline dihydrate is an antibiotic of the tetracycline class, acting as a potent inhibitor of both Gram-negative and Gram-positive bacteria. It functions by preventing the binding of aminoacyl-tRNA to the m-ribosomal RNA complex and also exhibits anti-HSV-1 activity. This compound is synthesized by a type II polyketide synthase from microorganisms, specifically *Streptomyces rimosus*.

  • Inhibits Gram-negative and Gram-positive bacteria
  • Acts as a protein synthesis inhibitor
  • Exhibits anti-HSV-1 activity
  • Light yellow to yellow solid appearance

ENCOMPASS_PREFERRED
11

Medchemexpress LLC Oxytetracycline dihydrate | 6153-64-6 | 99.4% | 1 G
SDP

Oxytetracycline dihydrate is an antibiotic belonging to the tetracycline class. It potently inhibits Gram-negative and Gram-positive bacteria. It acts as a protein synthesis inhibitor, preventing the binding of aminoacyl-tRNA to the m-ribosomal RNA complex. Additionally, it exhibits anti-HSV-1 activity.

  • Antibiotic belonging to the tetracycline class
  • Potent inhibitor of Gram-negative and Gram-positive bacteria
  • Protein synthesis inhibitor
  • Possesses anti-HSV-1 activity

ENCOMPASS_PREFERRED
12

Medchemexpress LLC Oxytetracycline dihydrate | 6153-64-6 | MFCD00151234 | 99.4% | 100 MG
SDP

Oxytetracycline dihydrate is an antibiotic of the tetracycline class that potently inhibits Gram-negative and Gram-positive bacteria. It acts as a protein synthesis inhibitor by preventing the binding of aminoacil-tRNA to the m-ribosomal RNA complex and also exhibits anti-HSV-1 activity.

  • Potently inhibits gram-negative and gram-positive bacteria
  • Acts as a protein synthesis inhibitor
  • Prevents the binding of aminoacil-tRNA to the m-ribosomal RNA complex
  • Exhibits anti-HSV-1 activity
  • Bacterial aromatic polyketide

ENCOMPASS_PREFERRED
13

Anhydrochlortetracycline hydrochloride, can be used as secondary standard, Thermo Scientific™

CAS: 65490-24-6 Molecular Formula: C22H22Cl2N2O7 Molecular Weight (g/mol): 497.325 MDL Number: MFCD00143616 InChI Key: ISGAAFMBTIWTEU-DTTSPEASSA-N Synonym: anhydrochlortetracycline hydrochloride,anhydro chlortetracycline hydrochloride,anhydro chlortetracycline,anhydroaureomycin hydrochloride,anhydrochlortetracyline hydrochloride,2z,4s,4as,12as-2-amino hydroxy methylidene-7-chloro-4-dimethylamino-10,11,12a-trihydroxy-6-methyl-4a,5-dihydro-4h-tetracene-1,3,12-trione hydrochloride,4s,12as,4as-4-dimethylamino-7-chloro-3,10,11,12a-tetrahydroxy-6-methyl-1,1 2-dioxo-4,5,12a,4a-tetrahydronaphthacene-2-carboxamide, chloride,4s,4as,12ar-7-chloro-4-dimethylamino-1,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide-hydrogen chloride 1/1,4s,4as,12as-7-chloro-4-dimethylamino-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide hydrochloride,4s,4as,12as-7-chloro-4-dimethylamino-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-4a,5-dihydro-4h-tetracene-2-carboxamide hydrochloride PubChem CID: 54710411 IUPAC Name: (4S,4aS,12aR)-7-chloro-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide;hydrochloride SMILES: CC1=C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C14)Cl)O)O)O)O)C(=O)N)N(C)C.Cl

PubChem CID 54710411
CAS 65490-24-6
Molecular Weight (g/mol) 497.325
MDL Number MFCD00143616
SMILES CC1=C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C14)Cl)O)O)O)O)C(=O)N)N(C)C.Cl
Synonym anhydrochlortetracycline hydrochloride,anhydro chlortetracycline hydrochloride,anhydro chlortetracycline,anhydroaureomycin hydrochloride,anhydrochlortetracyline hydrochloride,2z,4s,4as,12as-2-amino hydroxy methylidene-7-chloro-4-dimethylamino-10,11,12a-trihydroxy-6-methyl-4a,5-dihydro-4h-tetracene-1,3,12-trione hydrochloride,4s,12as,4as-4-dimethylamino-7-chloro-3,10,11,12a-tetrahydroxy-6-methyl-1,1 2-dioxo-4,5,12a,4a-tetrahydronaphthacene-2-carboxamide, chloride,4s,4as,12ar-7-chloro-4-dimethylamino-1,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide-hydrogen chloride 1/1,4s,4as,12as-7-chloro-4-dimethylamino-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide hydrochloride,4s,4as,12as-7-chloro-4-dimethylamino-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-4a,5-dihydro-4h-tetracene-2-carboxamide hydrochloride
IUPAC Name (4S,4aS,12aR)-7-chloro-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide;hydrochloride
InChI Key ISGAAFMBTIWTEU-DTTSPEASSA-N
Molecular Formula C22H22Cl2N2O7