Tretinoin

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

1971

www.ebi.ac.uk

First approval year: 1971
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Tretinoin
www.ebi.ac.uk

Molecular weight: 300.44
www.ebi.ac.uk

Structure (SMILES): CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1
www.ebi.ac.uk

acticin
Acticin
altreno
Altreno
atralin
Atralin
avita
Avita
renova
Renova
retin a
retin a micro
Retin-a
Retin-a micro
Retin-a-micro
tretin x
Tretin-x
tretinoin
Tretinoin
tretinoin component of solage
Tretinoin component of solage
tretinoin component of tri luma
Tretinoin component of tri-luma
tretinoin component of twyneo
Tretinoin component of twyneo

And 6 more, listed on the interactive page.

aberel
Aberel
All -trans Retinoic Acid (ATRA)
all trans retinoic acid
all trans Retinoic Acid
all trans retinoic acid (VESANOID)
all trans retinoic acid vesanoid
All trans-retinoic acid
all-trans retinoic acid
All-trans retinoic acid
All-trans Retinoic Acid
all-trans retinoic acid (ATRA)
All-trans retinoic acid (ATRA)
All-Trans Retinoic Acid (ATRA)
All-Trans Retinoic Acid (ATRA) Dose -1
All-Trans Retinoic Acid (ATRA) Dose 0
All-Trans Retinoic Acid (ATRA) Dose 1
All-Trans Retinoid Acid(ATRA)
All-trans-retinoic acid
Altreno
atra
atRA
Atra
ATRA
Atralin gel

And 66 more, listed on the interactive page.

CAS registry numbers

302-79-4

ChEMBL ID: CHEMBL38
www.ebi.ac.uk

InChIKey: SHGAZHPCJJPHSC-YCNIQYBTSA-N
www.ebi.ac.uk

PubChem compound IDs

444795

RxNorm IDs (RxCUI)

10753

FDA ingredient codes (UNII)

5688UTC01R

D10AD01
D10AD51
L01XF01

Sources for recorded values

www.ebi.ac.uk

Applicant: BAUSCH
Approval date: 26 Jan 1973
Application number: NDA017340

Patents: 2
Designations: 1
Earliest recorded loss of exclusivity: 22 Aug 2038
First in class: No
Fast track: No
Breakthrough designation: No
Orphan designation: No
Priority review: No
Orphan exclusivity: No
Accelerated approval: No
Availability: Prescription only
Boxed warning: Yes

Pharmacology name: tretinoin
Type: Metabolite
Drug name stem: -retin-
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Oral
topical

Action
Agonist
Action type
Agonist
Target
Retinoic acid receptor-α
Gene symbol
RARA
Protein identifier
P10276
Median affinity
9.4
Affinity units
pKd
Primary target
Yes
Action
Agonist
Action type
Agonist
Target
Retinoic acid receptor-β
Gene symbol
RARB
Protein identifier
P10826
Median affinity
7.92
Affinity units
pEC50
Primary target
Yes
Action
Agonist
Action type
Agonist
Target
Retinoic acid receptor-γ
Gene symbol
RARG
Protein identifier
P13631
Median affinity
9.6
Affinity units
pKd
Primary target
Yes
Action
Agonist
Action type
Agonist
Target
RAR-related orphan receptor-β
Gene symbol
RORB
Protein identifier
Q92753
Action
Agonist
Action type
Agonist
Target
TLX
Gene symbol
NR2E1
Protein identifier
Q9Y466
Median affinity
5.74
Affinity units
pEC50
Mechanism
Retinoic acid receptor agonist
Action type
Agonist
Target
Retinoic acid receptor
Protein identifier
P10276
Mechanism
Retinoic acid receptor agonist
Action type
Agonist
Target
Retinoic acid receptor
Protein identifier
P10826
Mechanism
Retinoic acid receptor agonist
Action type
Agonist
Target
Retinoic acid receptor
Protein identifier
P13631
Action
Antagonist
Action type
Antagonist
Target
RAR-related orphan receptor-β
Gene symbol
RORB
Protein identifier
Q92753
Median affinity
9.82
Affinity units
pIC50
Action
Full agonist
Action type
FULL_AGONIST
Target
Testicular receptor 4
Gene symbol
NR2C2
Protein identifier
P49116
Median affinity
4.62
Affinity units
pEC50
Action
Full agonist
Action type
FULL_AGONIST
Target
Peroxisome proliferator-activated receptor-β/δ
Gene symbol
PPARD
Protein identifier
Q03181
Median affinity
7.8
Affinity units
pKd

Open Targets mechanisms

Mechanism
Retinoic acid receptor agonist
Action type
Agonist
Target
Retinoic acid receptor

Action type
Agonist
Gene symbol
RARA
Protein identifier
P10276
Organism
Homo sapiens
Target development level
Clinical
Action type
Agonist
Gene symbol
RARB
Protein identifier
P10826
Organism
Homo sapiens
Target development level
Clinical
Action type
Agonist
Gene symbol
RARG
Protein identifier
P13631
Organism
Homo sapiens
Target development level
Clinical
Action type
Agonist
Gene symbol
NR2C2
Protein identifier
P49116
Organism
Homo sapiens
Action type
Agonist
Gene symbol
PPARD
Protein identifier
Q03181
Organism
Homo sapiens
Target development level
Chemical evidence
Action type
Agonist
Gene symbol
NR2E1
Protein identifier
Q9Y466
Organism
Homo sapiens
Target development level
Biological evidence
Action type
Antagonist
Gene symbol
RORB
Protein identifier
Q92753
Organism
Homo sapiens
Target development level
Chemical evidence

Condition
Myelodysplastic Syndromes
Highest recorded phase
3
Condition identifier
EFO:0000198
Subject identifier
D009190
Condition
Neoplasms, Plasma Cell
Highest recorded phase
1
Condition identifier
EFO:0000200
Subject identifier
D054219
Condition
Leukemia, Myeloid, Acute
Highest recorded phase
3
Condition identifier
EFO:0000222
Subject identifier
D015470
Condition
Leukemia, Promyelocytic, Acute
Highest recorded phase
4
Condition identifier
EFO:0000224
Subject identifier
D015473
Condition
Carcinoma, Adenoid Cystic
Highest recorded phase
2
Condition identifier
EFO:0000231
Subject identifier
D003528
Condition
Melanoma
Highest recorded phase
2
Condition identifier
EFO:0000389
Subject identifier
D008545
Condition
Emphysema
Highest recorded phase
2
Condition identifier
EFO:0000464
Subject identifier
D004646
Condition
Glioblastoma
Highest recorded phase
1
Condition identifier
EFO:0000519
Subject identifier
D005909
Condition
Leukemia
Highest recorded phase
3
Condition identifier
EFO:0000565
Subject identifier
D007938
Condition
Lymphoma
Highest recorded phase
2
Condition identifier
EFO:0000574
Subject identifier
D008223
Condition
Neoplasms
Highest recorded phase
4
Condition identifier
EFO:0000616
Subject identifier
D009369
Condition
Neuroblastoma
Highest recorded phase
2
Condition identifier
EFO:0000621
Subject identifier
D009447
Condition
Prostatic Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0000673
Subject identifier
D011471
Condition
Small Cell Lung Carcinoma
Highest recorded phase
2
Condition identifier
EFO:0000702
Subject identifier
D055752
Condition
Carcinoma, Squamous Cell
Highest recorded phase
3
Condition identifier
EFO:0000707
Subject identifier
D002294
Condition
Melanoma
Highest recorded phase
2
Condition identifier
EFO:0000756
Subject identifier
D008545
Condition
Multiple Myeloma
Highest recorded phase
2
Condition identifier
EFO:0001378
Subject identifier
D009101
Condition
Keratosis, Actinic
Highest recorded phase
2
Condition identifier
EFO:0002496
Subject identifier
D055623
Condition
Pancreatic Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0002618
Subject identifier
D010190
Condition
Carcinoma, Non-Small-Cell Lung
Highest recorded phase
3
Condition identifier
EFO:0003060
Subject identifier
D002289
Condition
Autistic Disorder
Highest recorded phase
0.5
Condition identifier
EFO:0003758
Subject identifier
D001321
Condition
Breast Neoplasms
Highest recorded phase
3
Condition identifier
EFO:0003869
Subject identifier
D001943
Condition
Acne Vulgaris
Highest recorded phase
4
Condition identifier
EFO:0003894
Subject identifier
D000152
Condition
Melanosis
Highest recorded phase
4
Condition identifier
EFO:0003963
Subject identifier
D008548
Condition
Carcinoma, Basal Cell
Highest recorded phase
3
Condition identifier
EFO:0004193
Subject identifier
D002280

And 20 more, listed on the interactive page.

Condition identifier
EFO_0000198
Highest recorded phase
2
Condition identifier
EFO_0000222
Highest recorded phase
3
Condition identifier
EFO_0000224
Condition identifier
EFO_0000231
Highest recorded phase
2
Condition identifier
EFO_0000389
Highest recorded phase
2
Condition identifier
EFO_0000565
Highest recorded phase
3
Condition identifier
EFO_0000574
Highest recorded phase
2
Condition identifier
EFO_0000616
Condition identifier
EFO_0000621
Highest recorded phase
2
Condition identifier
EFO_0000707
Highest recorded phase
3
Condition identifier
EFO_0000756
Highest recorded phase
2
Condition identifier
EFO_0001378
Highest recorded phase
2
Condition identifier
EFO_0002496
Highest recorded phase
2
Condition identifier
EFO_0002618
Highest recorded phase
2
Condition identifier
EFO_0003060
Highest recorded phase
3
Condition identifier
EFO_0003758
Condition identifier
EFO_0003869
Highest recorded phase
2
Condition identifier
EFO_0003894
Condition identifier
EFO_0003963
Condition identifier
EFO_0003963
Highest recorded phase
4
Condition identifier
EFO_0004193
Highest recorded phase
3
Condition identifier
EFO_0004198
Highest recorded phase
3
Condition identifier
EFO_0004199
Highest recorded phase
2
Condition identifier
EFO_0004208
Condition identifier
EFO_0004268
Highest recorded phase
2

And 77 more, listed on the interactive page.

Warning
Black Box Warning
Effect
carcinogenicity
Warning
Black Box Warning
Effect
hematological toxicity
Warning
Black Box Warning
Effect
teratogenicity

Warning
Black Box Warning
Effect
carcinogenicity
Country
United States
Warning
Black Box Warning
Effect
hematological toxicity
Country
United States
Warning
Black Box Warning
Effect
teratogenicity
Country
United States

Event
abortion induced
Reports
890
Reporting signal score
2,614.6
Event
abortion spontaneous
Reports
377
Reporting signal score
343.285
Event
acne
Reports
250
Reporting signal score
317.749
Event
acute myeloid leukaemia
Reports
35
Reporting signal score
82.859
Event
acute promyelocytic leukaemia
Reports
21
Reporting signal score
83.2886
Event
acute promyelocytic leukaemia differentiation syndrome
Reports
94
Reporting signal score
379.929
Event
benign intracranial hypertension
Reports
26
Reporting signal score
97.2983
Event
blepharospasm
Reports
16
Reporting signal score
43.9862
Event
blood triglycerides increased
Reports
592
Reporting signal score
1,339.57
Event
chapped lips
Reports
111
Reporting signal score
281.358
Event
cheilitis
Reports
169
Reporting signal score
387.347
Event
congenital knee dislocation
Reports
9
Reporting signal score
56.2007
Event
congenital musculoskeletal anomaly
Reports
9
Reporting signal score
34.7266
Event
depression
Reports
1,546
Reporting signal score
1,777.27
Event
diarrhoea
Reports
162
Reporting signal score
299.609
Event
differentiation syndrome
Reports
91
Reporting signal score
330.011
Event
dry skin
Reports
649
Reporting signal score
1,034.52
Event
dyspnoea
Reports
135
Reporting signal score
273.04
Event
electrocardiogram qt prolonged
Reports
34
Reporting signal score
32.9107
Event
fall
Reports
26
Reporting signal score
276.476
Event
febrile neutropenia
Reports
86
Reporting signal score
121.147
Event
haematopoietic neoplasm
Reports
6
Reporting signal score
33.1516
Event
hypercalcaemia
Reports
27
Reporting signal score
47.6231
Event
hyperleukocytosis
Reports
33
Reporting signal score
152.11
Event
idiopathic intracranial hypertension
Reports
44
Reporting signal score
194.784

And 20 more, listed on the interactive page.

NCT00000621
clinicaltrials.gov
NCT00002479
clinicaltrials.gov
NCT00005969
clinicaltrials.gov
NCT00002658
clinicaltrials.gov
NCT00002701
clinicaltrials.gov
NCT00005823
clinicaltrials.gov
NCT00005863
clinicaltrials.gov
NCT00006220
clinicaltrials.gov
NCT00006239
clinicaltrials.gov
NCT00016159
clinicaltrials.gov
NCT00276601
clinicaltrials.gov
NCT00482833
clinicaltrials.gov
NCT00492856
clinicaltrials.gov
NCT00528450
clinicaltrials.gov
NCT00551460
clinicaltrials.gov
NCT02177812
clinicaltrials.gov
NCT02273102
clinicaltrials.gov
NCT00003601
clinicaltrials.gov
NCT00003656
clinicaltrials.gov
NCT00100906
clinicaltrials.gov
NCT00003934
clinicaltrials.gov
NCT00180128
clinicaltrials.gov
NCT00378365
clinicaltrials.gov
NCT00408278
clinicaltrials.gov
NCT00413166
clinicaltrials.gov

And 127 more, listed on the interactive page.

Dose: 0.06%, or 0.08%
Route: Topical
How often: Once daily in the evening

Apply a thin layer
Keep away from eyes, mouth, nose creases, mucous membranes

Hydrogen bond acceptors: 1
Hydrogen bond donors: 1
Polar surface area: 37.3
Calculated partition coefficient (ALogP): 5.6
Calculated partition coefficient (XLogP): 6.3
Prodrug: No
Chirality: Achiral
Inorganic: No
Rule-of-five violations: 1
Rotatable bonds: 5
Heavy atoms: 22
Molecular formula: C20H28O2
Monoisotopic mass: 300.208930132
Natural product: Yes

0187-0005
0187-5140
0187-5144
0187-5146
0187-5148
0187-5150
0187-5160
0187-5162
0187-5164
0187-5170
0187-5172
0299-5945
0299-5950
0378-8082
0378-8083
0378-8084
0378-8085
0378-8086
0378-8090
0472-0117
0472-1790
0574-2201
0574-2205
0574-2225
0574-2301

And 66 more, listed on the interactive page.

Recorded assays: 5,977
Active assays: 620

Confirmatory
Other
Screening
Summary

Antineoplastic Agents
id.nlm.nih.gov
Keratolytic Agents
id.nlm.nih.gov

Distribution coefficient (LogD)

Median: 4.3
Mean: 4.3
Minimum: 4.3
Maximum: 4.3
Unit: unitless
Assays: 1
Standard deviation: 0
Summary method: median
Censored results excluded: 0
Other units excluded: 0
Unknown units excluded: 0

Measurement types

LogD

Oral bioavailability

Median: 25.205
Mean: 35.3075
Minimum: 0.82
Maximum: 90
Unit: %
Assays: 4
Standard deviation: 42.8843
Summary method: median
Censored results excluded: 0
Other units excluded: 0
Unknown units excluded: 0

Measurement types

Related records

Trials (219)

"AIDA" Protocol (LAP 0493)
90Y DOTA/Retinoic Acid for Neuroblastoma and Neuroendocrine Tumor (NET)
A Clinical Study Evaluating the Efficacy and Safety of Retinoic Acid in Patients With 15q11-q13 Duplication Syndrome
A Clinical Study on the Efficacy and Safety of All-trans Retinoic Acid Combined With VAC Regimen in the Treatment of Intermediate-to-high-risk Rhabdomyosarcoma
A Clinical Study to Evaluate the Safety and Effectiveness of an Investigational Product Called CT Gel
A Comparative Study of Adapalene Gel,0.3% Versus Tretinoin Emollient Cream, 0.05% for the Treatment of Photoaging
A Phase I Dose Escalation Study of GSK2879552 in Subjects With Acute Myeloid Leukemia (AML)
A Phase II Study of the Combination of Pembrolizumab and ATRA Combination Treatment of Relapsed HL and B-NHL
A Pilot Study of 5-AZA and ATRA for Prostate Cancer With PSA-only Recurrence After Local Treatment
A Pilot Study of the Combination of Retinoic Acid and Interferon-Alpha2a for the Treatment of Lymphoproliferative Disorders in Children With Immunodeficiency Syndromes
A Randomised Trial of ATRA in a Novel Drug Combination for Pancreatic Cancer
A Study Comparing Combination Clindamycin Phosphate/Tretinoin Gel Alone Versus With Benzoyl Peroxide Foaming Cloths for Facial Acne
A Study Comparing Tretinoin Cream 0.025% and RETIN-A® Cream 0.025% in the Treatment of Acne Vulgaris
A Study Comparing Tretinoin Gel Microsphere, 0.04% and RETIN-A MICRO ® Gel Microsphere, 0.04% in the Treatment of Acne Vulgaris
A Study Comparing Tretinoin Gel Microsphere, 0.1% and RETIN-A MICRO ® Gel Microsphere, 0.1% in the Treatment of Acne Vulgaris
A Study for Improving the Outcome of Childhood Acute Promyeloid Leukemia
A Study of Acne Treatment in Children Ages 9 to 11
A Study of All-Trans Retinoic Acid (ATRA) and Bryostatin in Patients With Acute Myeloid Leukemia (AML) and Myelodysplastic Syndrome (MDS)
A Study of ATRA in the Treatment of ITP
A Study of Bomedemstat (IMG-7289/MK-3543) With and Without ATRA, in Participants With Advanced Myeloid Malignancies (IMG-7289-CTP-101/MK-3543-001)

Approved for (4)

Acne
Acute promyelocytic leukemia
Hyperpigmentation of the skin
Neoplasm

In development for (38)

Actinic keratosis Phase 2
Acute myeloid leukemia Phase 3
Adenoid cystic carcinoma Phase 2
Amyotrophic lateral sclerosis Phase 1
Anemia Phase 2
Anti-neutrophil antibody associated vasculitis Phase 2
Autism Early phase 1
Autoimmune thrombocytopenia Phase 3
Autoimmune thrombocytopenic purpura Phase 3
Basal cell carcinoma Phase 3
Bone marrow neoplasm Phase 3
Breast cancer Phase 3
Breast neoplasm Phase 3
Colorectal cancer Phase 2
COVID-19 Phase 2
Cutaneous melanoma Phase 2
Exocrine pancreatic carcinoma Phase 2
Glioblastoma Phase 1
Hematopoietic and lymphoid cell neoplasm Phase 1
Kidney cancer Phase 2

Targets (3)

RARA Retinoic acid receptor agonist
RARB Retinoic acid receptor agonist
RARG Retinoic acid receptor agonist

Tretinoin

Development status

Names and chemistry

Brand names (31)

Other names (91)

Identifiers

ATC classification codes (3)

Regulatory information

United States

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action (11)

Open Targets mechanisms

DrugCentral mechanisms (7)

Investigated indications (45)

Open Targets indications (102)

Warnings (3)

Open Targets warnings (3)

Reported adverse events (45)

Trial references (152)

Dosing

Conditions of use (2)

Chemical properties

National Drug Codes

Evidence counts

Active assay types (4)

Pharmacologic actions

Biological measurements

Observed measurements

Distribution coefficient (LogD)

Measurement types

Oral bioavailability

Measurement types

Related records

Trials (219)

Approved for (4)

In development for (38)

Other linked conditions (2)

Targets (3)