DOXYCYCLINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1967)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A01AB22
UNII: N12000U13O

Structure
InChI Key XQTWDDCIUJNLTR-CVHRZJFOSA-N
Smile C[C@H]1c2cccc(O)c2C(=O)C2=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3[C@@H](O)[C@@H]21.O
InChI
InChI=1S/C22H24N2O8.H2O/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;/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31);1H2/t7-,10+,14+,15-,17-,22-;/m0./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H26N2O9
Molecular Weight 462.46
AlogP -0.35
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 2.0
Polar Surface Area 181.62
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 32.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -0.02 - EXP
Henry's Law Constant 4.66E-24 atm-m3/mole EST
Atmospheric OH Rate Constant 2.66E-10 cm3/molecule-sec EST
Water Solubility 630 mg/L EXP
Vapor Pressure 1.42E-23 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Bacterial 70S ribosome inhibitor PubMed DailyMed
Primary Target
MMP7

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Anthrax 4 D000881 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 3 D029424 ClinicalTrials
Elephantiasis, Filarial 3 D004605 ClinicalTrials
Persian Gulf Syndrome 3 D018923 ClinicalTrials
Scrub Typhus 3 D012612 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Lyme Disease 3 D008193 ClinicalTrials
Arthritis, Reactive 3 D016918 ClinicalTrials
Urethritis 3 D014526 ClinicalTrials
Pleural Effusion 3 D010996 ClinicalTrials
Syphilis 3 D013587 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
Chlamydia Infections 3 D002690 ClinicalTrials
Eczema 2 D004485 ClinicalTrials
Amyloidosis, Familial 2 D028226 ClinicalTrials
Squamous Cell Carcinoma of Head and Neck 2 D000077195 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Plague 2 D010930 ClinicalTrials
Diabetic Retinopathy 2 D003930 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Pain 2 D010146 ClinicalTrials
Aortic Aneurysm, Abdominal 2 D017544 ClinicalTrials
Marfan Syndrome 2 D008382 ClinicalTrials
Amyloidosis 2 D000686 ClinicalTrials
Dry Eye Syndromes 2 D015352 ClinicalTrials
Myocardial Infarction 2 D009203 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Seizures 2 D012640 ClinicalTrials
Diabetic Foot 2 D017719 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Dermatitis, Atopic 2 D003876 ClinicalTrials
Crohn Disease 2 D003424 ClinicalTrials
Adenomatous Polyposis Coli 2 D011125 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Mansonelliasis 2 D008368 ClinicalTrials
Sezary Syndrome 2 D012751 ClinicalTrials
Mycosis Fungoides 2 D009182 ClinicalTrials
Pelvic Inflammatory Disease 2 D000292 ClinicalTrials
Graves Ophthalmopathy 2 D049970 ClinicalTrials
Eye Burns 2 D005126 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Cystic Fibrosis 2 D003550 ClinicalTrials
Reperfusion Injury 2 D015427 ClinicalTrials
Lichen Planus, Oral 2 D017676 ClinicalTrials
Blepharitis 2 D001762 ClinicalTrials
Aneurysm 2 D000783 ClinicalTrials
Amyloidosis 2 D000686 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Osteomyelitis 0 D010019 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 0 D016410 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 28.1
Nervous system disorders Headache 27.3
Nervous system disorders Headache
Nervous system disorders Headache 25.8
Infections and infestations Nasopharyngitis 25.5
Infections and infestations Rhinitis 25.5
Infections and infestations Nasopharyngitis 25.2
Infections and infestations Rhinitis 25.2
Nervous system disorders Headache 23.8
General disorders and administration site conditions Discomfort 23.0
General disorders and administration site conditions Pain 23.0
General disorders and administration site conditions Tenderness 23.0
Infections and infestations Nasopharyngitis 22.1
Infections and infestations Rhinitis 22.1
Infections and infestations Nasopharyngitis
Infections and infestations Rhinitis
General disorders and administration site conditions Discomfort 21.0
General disorders and administration site conditions Pain 21.0
General disorders and administration site conditions Tenderness 21.0
Infections and infestations Influenza
General disorders and administration site conditions Discomfort 18.1
General disorders and administration site conditions Pain 18.1
General disorders and administration site conditions Tenderness 18.1
Gastrointestinal disorders Toothache 18.1
Infections and infestations Nasopharyngitis 16.7
Infections and infestations Rhinitis 16.7
Gastrointestinal disorders Toothache 14.3
Gastrointestinal disorders Nausea 13.4
Gastrointestinal disorders Toothache
Infections and infestations Influenza 11.3
Infections and infestations Infection 10.9
Gastrointestinal disorders Tooth abscess 10.9
Infections and infestations Infection 9.9
Gastrointestinal disorders Tooth abscess 9.9
Gastrointestinal disorders Tooth abscess
Gastrointestinal disorders Tooth disorder
Infections and infestations Infection 8.6
Gastrointestinal disorders Tooth abscess 8.6
Sensitivity of teeth 8.5
Infections and infestations Sinusitis
Gastrointestinal disorders Vomiting 8.13
Gastrointestinal disorders Nausea 7.98
Sensitivity of teeth 7.7
Respiratory, thoracic and mediastinal disorders Upper-airway cough syndrome 7.7
Sensitivity of teeth 6.7
Gastrointestinal disorders Toothache 6.57
Gastrointestinal disorders Oropharyngeal discomfort 6.5
Gastrointestinal disorders Oropharyngeal pain 6.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 6.4
Musculoskeletal and connective tissue disorders Myalgia 6.4
Musculoskeletal and connective tissue disorders Back pain 6.2
Skin and subcutaneous tissue disorders Erythema 6.2
Gastrointestinal disorders Oral pain 6.2
General disorders and administration site conditions Pain 6.2
Respiratory, thoracic and mediastinal disorders Cough 6.1
Gastrointestinal disorders Dyspepsia 6.1
Gastrointestinal disorders Tooth disorder 6.1
Gastrointestinal disorders Oropharyngeal discomfort
Gastrointestinal disorders Oropharyngeal pain
Gastrointestinal disorders Gingivitis 5.8
General disorders and administration site conditions Swelling 5.8
Gastrointestinal disorders Gingivitis 5.7
Gastrointestinal disorders Oropharyngeal discomfort 5.7
Gastrointestinal disorders Oropharyngeal pain 5.7
General disorders and administration site conditions Swelling 5.7
Gastrointestinal disorders Tooth fracture 5.7
Musculoskeletal and connective tissue disorders Arthralgia 5.63
Gastrointestinal disorders Diarrhoea 5.63
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.63
Respiratory, thoracic and mediastinal disorders Upper-airway cough syndrome 5.6
Gastrointestinal disorders Nausea
Musculoskeletal and connective tissue disorders Back pain 5.3
Skin and subcutaneous tissue disorders Erythema 5.3
Gastrointestinal disorders Oral pain 5.3
General disorders and administration site conditions Pain 5.3
Infections and infestations Sinusitis 5.3
Gastrointestinal disorders Oropharyngeal discomfort 5.16
Gastrointestinal disorders Oropharyngeal pain 5.16
Respiratory, thoracic and mediastinal disorders Sinus congestion 5.16
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Sinus congestion
Gastrointestinal disorders Tooth fracture 5.1
Respiratory, thoracic and mediastinal disorders Upper-airway cough syndrome 4.8
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.6
Musculoskeletal and connective tissue disorders Myalgia 4.6
Psychiatric disorders Premenstrual syndrome 4.4
Skin and subcutaneous tissue disorders Erythema 4.3
Gastrointestinal disorders Oral pain 4.3
General disorders and administration site conditions Pain 4.3
Respiratory, thoracic and mediastinal disorders Cough 4.23
Reproductive system and breast disorders Dysmenorrhoea 4.23
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Abdominal discomfort 4.1
Gastrointestinal disorders Abdominal pain 4.1
Gastrointestinal disorders Abdominal pain upper 4.1
Gastrointestinal disorders Dyspepsia 4.1
Gastrointestinal disorders Gingivitis 4.1
General disorders and administration site conditions Swelling 4.1
Gastrointestinal disorders Tooth fracture 4.1
Gastrointestinal disorders Abdominal discomfort 3.8
Gastrointestinal disorders Abdominal pain 3.8
Gastrointestinal disorders Abdominal pain upper 3.8
Gastrointestinal disorders Dyspepsia 3.8
Skin and subcutaneous tissue disorders Dermatitis 3.76
Gastrointestinal disorders Dyspepsia 3.76
General disorders and administration site conditions Pain 3.76
Skin and subcutaneous tissue disorders Rash 3.76
Nervous system disorders Sinus headache 3.76
Gastrointestinal disorders Tooth abscess 3.76
Musculoskeletal and connective tissue disorders Arthralgia
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Diarrhoea
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Nervous system disorders Sinus headache
Gastrointestinal disorders Abdominal discomfort 3.6
Gastrointestinal disorders Abdominal pain 3.6
Gastrointestinal disorders Abdominal pain upper 3.6
Musculoskeletal and connective tissue disorders Back pain 3.6
Respiratory, thoracic and mediastinal disorders Cough 3.6
Gastrointestinal disorders Dyspepsia 3.6
Nervous system disorders Insomnia 3.4
Gastrointestinal disorders Diarrhoea 3.3
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.3
Musculoskeletal and connective tissue disorders Myalgia 3.3
Gastrointestinal disorders Oropharyngeal discomfort 3.3
Gastrointestinal disorders Oropharyngeal pain 3.3
Psychiatric disorders Premenstrual syndrome 3.3
Musculoskeletal and connective tissue disorders Back pain 3.29
Infections and infestations Bronchitis 3.29
Infections and infestations Sinusitis 3.29
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Diarrhoea 3.25
Infections and infestations Vaginal infection 3.25
Vaginitis bacterial 3.25
Psychiatric disorders Premenstrual syndrome 3.1
Musculoskeletal and connective tissue disorders Back pain 2.9
Nervous system disorders Insomnia 2.9
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Gingival pain
Infections and infestations Infection
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Skin and subcutaneous tissue disorders Rash
Infections and infestations Sinusitis 2.7
Respiratory, thoracic and mediastinal disorders Cough 2.4
Gastrointestinal disorders Diarrhoea 2.4
Gastrointestinal disorders Gingival bleeding 2.4
Metabolism and nutrition disorders Osteopenia 2.4
General disorders and administration site conditions Pain 2.4
Infections and infestations Bronchitis
Reproductive system and breast disorders Dysmenorrhoea
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Pain
Infections and infestations Bronchitis 2.3
General disorders and administration site conditions Pain 2.2
Gastrointestinal disorders Abdominal pain upper 2.03
Nervous system disorders Headache 2.03
Infections and infestations Vulvovaginal mycotic infection 2.03
Metabolism and nutrition disorders Osteopenia 2.0
Investigations Body temperature increased 1.9
Infections and infestations Bronchitis 1.9
Infections and infestations Ear infection 1.9
Immune system disorders Hypersensitivity 1.9
Musculoskeletal and connective tissue disorders Neck pain 1.9
Musculoskeletal and connective tissue disorders Pain in jaw 1.9
Infections and infestations Sinusitis 1.9
Gastrointestinal disorders Tooth abscess 1.9
Musculoskeletal and connective tissue disorders Back pain 1.88
Infections and infestations Infection 1.88
Gastrointestinal disorders Nausea 1.8
Nervous system disorders Tension headache 1.8
Gastrointestinal disorders Vomiting 1.8
Aphthous stomatitis 1.7
Musculoskeletal and connective tissue disorders Back pain 1.7
Musculoskeletal and connective tissue disorders Neck pain 1.7
Musculoskeletal and connective tissue disorders Back pain 1.6
Infections and infestations Ear infection 1.6
Vascular disorders Hypertension 1.6
General disorders and administration site conditions Pain 1.6
General disorders and administration site conditions Tenderness 1.6
Infections and infestations Abscess 1.5
Musculoskeletal and connective tissue disorders Fistula 1.5
Nervous system disorders Insomnia 1.5
General disorders and administration site conditions Pain 1.5
Gastrointestinal disorders Pulpitis dental 1.5
Gastrointestinal disorders Tooth abscess 1.5
Gastrointestinal disorders Tooth loss 1.5
Aphthous stomatitis 1.4
General disorders and administration site conditions Pain 1.4
General disorders and administration site conditions Tenderness 1.4
General disorders and administration site conditions Inflammation 1.3
Musculoskeletal and connective tissue disorders Neck pain 1.3
Infections and infestations Skin infection 1.3
General disorders and administration site conditions Pain 1.2
General disorders and administration site conditions Tenderness 1.2
Musculoskeletal and connective tissue disorders Pain in jaw 1.1
Investigations Body temperature increased 1.0
Infections and infestations Bronchitis 1.0
Gastrointestinal disorders Diarrhoea 1.0
Musculoskeletal and connective tissue disorders Fistula 1.0
Gastrointestinal disorders Gingival bleeding 1.0
Immune system disorders Hypersensitivity 1.0
General disorders and administration site conditions Inflammation 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal pain 1.0
Infections and infestations Skin infection 1.0
Nervous system disorders Tension headache 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.939
Musculoskeletal and connective tissue disorders Myalgia 0.939
Musculoskeletal and connective tissue disorders Fistula 0.8
Gastrointestinal disorders Tooth loss 0.8
Aphthous stomatitis 0.7
Gastrointestinal disorders Gingival bleeding 0.7
Gastrointestinal disorders Nausea 0.7
Metabolism and nutrition disorders Osteopenia 0.7
Nervous system disorders Tension headache 0.7
Gastrointestinal disorders Vomiting 0.7
Infections and infestations Abscess 0.5
Gastrointestinal disorders Nausea 0.5
Musculoskeletal and connective tissue disorders Pain in jaw 0.5
Gastrointestinal disorders Pulpitis dental 0.5
Gastrointestinal disorders Tooth abscess 0.5
Gastrointestinal disorders Vomiting 0.5
Gastrointestinal disorders Gingival pain 0.469
Vascular disorders Hypertension 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.71
Gastrointestinal disorders
12.65
Skin and subcutaneous tissue disorders
11.56
Nervous system disorders
9.08
Immune system disorders
6.8
Psychiatric disorders
5.19
Respiratory, thoracic and mediastinal disorders
4.86
Vascular disorders
4.43
Injury, poisoning and procedural complications
4.34
Cardiac disorders
4.27
Infections and infestations
3.25
Musculoskeletal and connective tissue disorders
2.95
Investigations
2.71
Blood and lymphatic system disorders
2.42
Eye disorders
2.3
Metabolism and nutrition disorders
2.3
Renal and urinary disorders
2.17

Cross References

Resources Reference
CAS NUMBER 564-25-0
ChEBI 60648
ChEMBL CHEMBL1200699
FDA SRS N12000U13O
Guide to Pharmacology 6464
SureChEMBL SCHEMBL3155
CONTENTS